U.S. patent number 10,680,195 [Application Number 15/289,817] was granted by the patent office on 2020-06-09 for organic light-emitting device.
This patent grant is currently assigned to Samsung Display Co., Ltd.. The grantee listed for this patent is Samsung Display Co., Ltd.. Invention is credited to Naoyuki Ito, Seulong Kim, Younsun Kim, Jungsub Lee, Jino Lim, Dongwoo Shin.
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United States Patent |
10,680,195 |
Kim , et al. |
June 9, 2020 |
Organic light-emitting device
Abstract
An organic light emitting device includes: a first electrode; a
second electrode facing the first electrode; m emission units
stacked between the first electrode and the second electrode; and
m-1 charge generating layer(s) between the two adjacent emission
units from among the m emission units, m-1 charge generating
layer(s) including m-1 n-type charge generating layer(s) and m-1
p-type charge generating layer(s), wherein m is an integer of 2 or
greater, a maximum emission wavelength of light emitted from at
least one of the m emission units differs from that of light
emitted from at least one of the other emission units, at least one
of the m-1 n-type charge generating layer(s) includes a
metal-containing material and an electron transporting
metal-non-containing material.
Inventors: |
Kim; Younsun (Yongin-si,
KR), Kim; Seulong (Yongin-si, KR), Shin;
Dongwoo (Yongin-si, KR), Lee; Jungsub (Yongin-si,
KR), Ito; Naoyuki (Yongin-si, KR), Lim;
Jino (Yongin-si, KR) |
Applicant: |
Name |
City |
State |
Country |
Type |
Samsung Display Co., Ltd. |
Yongin-si, Gyeonggi-do |
N/A |
KR |
|
|
Assignee: |
Samsung Display Co., Ltd.
(Yongin-si, KR)
|
Family
ID: |
59787124 |
Appl.
No.: |
15/289,817 |
Filed: |
October 10, 2016 |
Prior Publication Data
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|
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Document
Identifier |
Publication Date |
|
US 20170263876 A1 |
Sep 14, 2017 |
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Foreign Application Priority Data
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Mar 10, 2016 [KR] |
|
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10-2016-0029093 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
H01L
51/5278 (20130101); H01L 51/508 (20130101); H01L
51/5076 (20130101); H01L 51/0072 (20130101); H01L
51/0081 (20130101); H01L 51/0067 (20130101) |
Current International
Class: |
H01L
51/50 (20060101); H01L 51/52 (20060101); H01L
51/00 (20060101) |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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10-2009-0119746 |
|
Nov 2009 |
|
KR |
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10-2013-0064661 |
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Jun 2013 |
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KR |
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10-2013-0135161 |
|
Dec 2013 |
|
KR |
|
10-2014-0119990 |
|
Oct 2014 |
|
KR |
|
Other References
Organic Electronics, 10, (2009), pp. 515-520. (Year: 2009). cited
by examiner.
|
Primary Examiner: Garrett; Dawn L
Attorney, Agent or Firm: Lewis Roca Rothgerber Christie
LLP
Claims
What is claimed is:
1. An organic light emitting device comprising: a first electrode;
a second electrode facing the first electrode; m emission units
stacked between the first electrode and the second electrode; and
m-1 charge generating layer(s) between each of the two adjacent
emission units from among the m emission units, m-1 charge
generating layer(s) comprising m-1 n-type charge generating
layer(s) and m-1 p-type charge generating layer(s), wherein m is an
integer of 2 or greater, a maximum emission wavelength of light
emitted from at least one of the m emission units differs from that
of light emitted from at least one of the other emission units, at
least one of the m-1 n-type charge generating layer(s) comprises a
metal-containing material and an electron transporting
metal-non-containing material, the metal-containing material
comprised in the m-1 n-type charge generating layer(s) comprises a
metal, a metal complex, or a combination thereof, the metal
comprised in the m-1 n-type charge generating layer(s) comprises
lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd),
promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd),
terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium
(Tm), ytterbium (Yb), and lutetium (Lu), or a combination thereof,
and the metal complex comprised in the m-1 n-type charge generating
layer(s) comprises an alkali metal, an alkaline earth metal, a
rare-earth metal, a transition metal, a late transition metal, or a
combination thereof, and at least one organic ligand selected from
a hydroxyquinoline, a hydroxyisoquinoline, a hydroxy
benzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a
hydroxyphenyl oxazole, a hydroxyphenyl thiazole, a hydroxydiphenyl
oxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl
pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenyl
benzothiazole, a bipyridine, a phenanthroline, and a
cyclopentadiene, and the organic light emitting device further
comprises: an electron transport layer between the second electrode
and an emission unit adjacent to the second electrode from among
the m emission units, wherein the electron transport layer
comprises a metal-containing material and an electron transporting
metal-non-containing material, the metal-containing material
comprised in the electron transport layer comprises a metal, a
metal complex, or a combination thereof, the metal comprised in the
electron transport layer comprises an alkali metal, an alkaline
earth metal, a rare-earth metal, a transition metal, a late
transition metal, or a combination thereof, the metal complex
comprised in the electron transport layer comprises an alkali
metal, an alkaline earth metal, a rare-earth metal, a transition
metal, a late transition metal, or a combination thereof, the
electron transporting metal-non-containing material is an organic
compound comprising at least one selected from a phenanthroline
ring, an imidazole ring, a pyridine ring, a pyrazine ring, a
pyrimidine ring, a pyridazine ring, and a triazine ring, and the
electron transporting metal-non-containing material comprised in
the electron transport layer does not include the following
compounds: ##STR00068## wherein the metal-containing material
comprised in the at least one of the m-1 n-type charge generating
layer(s) differs from the metal-containing material comprised in
the electron transport layer; the electron transporting
metal-non-containing material comprised in the at least one of the
m-1 n-type charge generating layer(s) differs from the electron
transporting metal-non-containing material comprised in the
electron transport layer; or the metal-containing material
comprised in the at least one of the m-1 n-type charge generating
layer(s) differs from the metal-containing material comprised in
the electron transport layer, and the electron transporting
metal-non-containing material comprised in the at least one of the
m-1 n-type charge generating layer(s) differs from the electron
transporting metal-non-containing material comprised in the
electron transport layer; and at least one of the m-1 n-type charge
generating layer(s) and the electron transporting layer does not
include a metal complex comprising lithium (Li).
2. The organic light-emitting device of claim 1, wherein when the
metal-containing material comprised in the at least one of the m-1
n-type charge generating layer(s) comprises the metal, the metal is
Yb.
3. The organic light-emitting device of claim 1, wherein when the
metal-containing material comprised in the at least one of the m-1
n-type charge generating layer(s) comprises the metal complex, the
metal complex comprises a metal selected from lithium (Li),
aluminum (Al), titanium (Ti), zirconium (Zr), hafnium (Hf), zinc
(Zn), and copper (Cu).
4. The organic light-emitting device of claim 1, wherein when the
metal-containing material comprised in the at least one of the m-1
n-type charge generating layer(s) comprises the metal complex, the
metal complex is a Li complex and/or an Al complex.
5. The organic light-emitting device of claim 1, wherein when the
metal-containing material comprised in the at least one of the m-1
n-type charge generating layer(s) comprises the metal complex, the
metal complex is lithium quinolate (Liq) or aluminum quinolate
(Alq3).
6. The organic light-emitting device of claim 1, wherein a lowest
unoccupied molecular orbital (LUMO) energy level of the electron
transporting metal-non-containing material is about -4.0 electron
volts (eV) or greater.
7. The organic light-emitting device of claim 1, wherein the
electron transporting metal-non-containing material is an organic
compound comprising at least one .pi. electron-depleted
nitrogen-containing ring.
8. The organic light-emitting device of claim 1, wherein when the
metal-containing material comprises the metal, a weight ratio of
the metal to the electron transporting metal-non-containing
material is in a range of about 0.01:100 to about 15:100.
9. The organic light-emitting device of claim 1, wherein when the
metal-containing material comprises the metal complex, a weight
ratio of the metal complex to the electron transporting
metal-non-containing material is in a range of about 1:100 to about
100:1.
10. The organic light-emitting device of claim 1, further
comprising: a hole transport region between the first electrode and
an emission unit adjacent to the first electrode from among the m
emission units, and a p-dopant in the hole transport region, the
LUMO energy level of the hole transport region being about -3.5 eV
or less.
11. An organic light emitting device comprising: a first electrode;
a second electrode facing the first electrode; m emission units
stacked between the first electrode and the second electrode; and
m-1 charge generating layer(s) between each of the two adjacent
emission units from among the m emission units, m-1 charge
generating layer(s) comprising m-1 n-type charge generating
layer(s) and m-1 p-type charge generating layer(s), wherein a
maximum emission wavelength of light emitted from at least one of
the m emission units differs from that of light emitted from at
least one of the other emission units, at least one of the m-1
n-type charge generating layer(s) comprises a metal-containing
material and an electron transporting metal-non-containing
material, the metal-containing material comprised in the m-1 n-type
charge generating layer(s) comprises a metal, a metal complex, or a
combination thereof, the metal comprised in the m-1 n-type charge
generating layer(s) comprises lanthanum (La), cerium (Ce),
praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm),
europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy),
holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and
lutetium (Lu), or a combination thereof, and the metal complex
comprised in the m-1 n-type charge generating layer(s) comprises an
alkali metal, an alkaline earth metal, a rare-earth metal, a
transition metal, a late transition metal, or a combination
thereof, and at least one organic ligand selected from a
hydroxyquinoline, a hydroxyisoquinoline, a hydroxy benzoquinoline,
a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl
oxazole, a hydroxyphenyl thiazole, a hydroxydiphenyl oxadiazole, a
hydroxydiphenyl thiadiazole, a hydroxyphenyl pyridine, a
hydroxyphenyl benzimidazole, a hydroxyphenyl benzothiazole, a
bipyridine, a phenanthroline, and a cyclopentadiene, and the
organic light emitting device further comprises: an electron
transport layer between the second electrode and an emission unit
adjacent to the second electrode from among the m emission units,
wherein the electron transport layer comprises a metal-containing
material and an electron transporting metal-non-containing
material, the metal-containing material comprised in the electron
transport layer comprises a metal, a metal complex, or a
combination thereof, the metal comprised in the electron transport
layer comprises an alkali metal, an alkaline earth metal, a
rare-earth metal, a transition metal, a late transition metal, or a
combination thereof, the metal complex comprised in the electron
transport layer comprises an alkali metal, an alkaline earth metal,
a rare-earth metal, a transition metal, a late transition metal, or
a combination thereof, the electron transporting
metal-non-containing material is an organic compound comprising at
least one selected from a phenanthroline ring, an imidazole ring, a
pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine
ring, and a triazine ring, and the electron transporting
metal-non-containing material comprised in the electron transport
layer does not include the following compounds: ##STR00069##
wherein m is an integer of 3 or greater, the m-1 n-type charge
generating layer(s) all comprise the same metal-containing material
and the same electron transporting metal-non-containing material,
and the metal-containing material comprised in the m-1 n-type
charge generating layer(s) differs from the metal-containing
material comprised in the electron transport layer; the electron
transporting metal-non-containing material comprised in the m-1
n-type charge generating layer(s) differs from the electron
transporting metal-non-containing material comprised in the
electron transport layer; or the metal-containing material
comprised in the m-1 n-type charge generating layer(s) differs from
the metal-containing material comprised in the electron transport
layer, and the electron transporting metal-non-containing material
comprised in the m-1 n-type charge generating layer(s) differs from
the electron transporting metal-non-containing material comprised
in the electron transport layer.
12. The organic light-emitting device of claim 1, wherein m is 2 or
3.
13. An organic light emitting device comprising: a first electrode;
a second electrode facing the first electrode; m emission units
stacked between the first electrode and the second electrode; and
m-1 charge generating layer(s) between each of the two adjacent
emission units from among the m emission units, m-1 charge
generating layer(s) comprising m-1 n-type charge generating
layer(s) and m-1 p-type charge generating layer(s), wherein m is an
integer of 2 or greater, a maximum emission wavelength of light
emitted from at least one of the m emission units differs from that
of light emitted from at least one of the other emission units, at
least one of the m-1 n-type charge generating layer(s) consists of
a metal-containing material and an electron transporting
metal-non-containing material the metal-containing material in the
m-1 n-type charge generating layer(s) consists of a metal, a metal
complex, or a combination thereof, the metal in the m-1 n-type
charge generating layer(s) consists of lanthanum (La), cerium (Ce),
praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm),
europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy),
holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and
lutetium (Lu), or a combination thereof, and the metal complex in
the m-1 n-type charge generating layer(s) consists of an alkali
metal, an alkaline earth metal, a rare-earth metal, a transition
metal, a late transition metal, or a combination thereof, and at
least one organic ligand selected from a hydroxyquinoline, a
hydroxyisoquinoline, a hydroxy benzoquinoline, a hydroxyacridine, a
hydroxyphenanthridine, a hydroxyphenyl oxazole, a hydroxyphenyl
thiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl
thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl
benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a
phenanthroline, and a cyclopentadiene, and the organic light
emitting device further comprises: an electron transport layer
between the second electrode and an emission unit adjacent to the
second electrode from among the m emission units, wherein the
electron transport layer comprises a metal-containing material and
an electron transporting metal-non-containing material, the
metal-containing material comprised in the electron transport layer
comprises a metal, a metal complex, or a combination thereof, the
metal comprised in the electron transport layer comprises an alkali
metal, an alkaline earth metal, a rare-earth metal, a transition
metal, a late transition metal, or a combination thereof, the metal
complex comprised in the electron transport layer comprises an
alkali metal, an alkaline earth metal, a rare-earth metal, a
transition metal, a late transition metal, or a combination
thereof, the electron transporting metal-non-containing material is
an organic compound comprising at least one selected from a
phenanthroline ring, an imidazole ring, a pyridine ring, a pyrazine
ring, a pyrimidine ring, a pyridazine ring, and a triazine ring,
and the electron transporting metal-non-containing material
comprised in the electron transport layer does not include the
following compounds: ##STR00070## wherein the metal-containing
material comprised in the at least one of the m-1 n-type charge
generating layer(s) differs from the metal-containing material
comprised in the electron transport layer; the electron
transporting metal-non-containing material comprised in the at
least one of the m-1 n-type charge generating layer(s) differs from
the electron transporting metal-non-containing material comprised
in the electron transport layer; or the metal-containing material
comprised in the at least one of the m-1 n-type charge generating
layer(s) differs from the metal-containing material comprised in
the electron transport layer, and the electron transporting
metal-non-containing material comprised in the at least one of the
m-1 n-type charge generating layer(s) differs from the electron
transporting metal-non-containing material comprised in the
electron transport layer; and at least one of the m-1 n-type charge
generating layer(s) and the electron transporting layer does not
include a metal complex comprising lithium (Li).
Description
CROSS-REFERENCE TO RELATED APPLICATION
This application claims priority to and the benefit of Korean
Patent Application No. 10-2016-0029093, filed on Mar. 10, 2016, in
the Korean Intellectual Property Office, the entire content of
which is incorporated herein by reference.
BACKGROUND
1. Field
One or more aspects of embodiments of the present disclosure relate
to an organic light-emitting device.
2. Description of the Related Art
Organic light emitting devices are self-emission devices that have
wide viewing angles, high contrast ratios, short response times,
and excellent brightness, driving voltage, and response speed
characteristics, and can produce full-color images.
An organic light-emitting device may include a first electrode on a
substrate, and a hole transport region, an emission layer, an
electron transport region, and a second electrode, which are
sequentially positioned on the first electrode. Holes provided
from, for example, the first electrode may move toward the emission
layer through the hole transport region, and electrons provided
from, for example, the second electrode may move toward the
emission layer through the electron transport region. Carriers,
such as holes and electrons, may then recombine in the emission
layer to produce excitons. These excitons transition from an
excited state to a ground state, thereby generating light.
SUMMARY
One or more aspects of embodiments of the present disclosure are
directed toward an organic light-emitting device having low driving
voltage, high efficiency, and long lifespan.
Additional aspects will be set forth in part in the description
which follows and, in part, will be apparent from the description,
or may be learned by practice of the presented embodiments.
According to one or more embodiments, an organic light-emitting
device includes a first electrode;
a second electrode facing the first electrode;
m emission units stacked between the first electrode and the second
electrode; and
m-1 charge generating layer(s) between each of the two adjacent
emission units from among the m emission units, the m-1 charge
generating layer(s) including m-1 n-type charge generating layer(s)
and m-1 p-type charge generating layer(s),
wherein the m is an integer of 2 or greater,
a maximum emission wavelength of light emitted from at least one of
the m emission units differs from that of light emitted from at
least one of the other emission units,
at least one of the m-1 n-type charge generating layer(s) includes
a metal-containing material and an electron transporting
metal-non-containing material,
wherein the metal-containing material is selected from a metal, a
metal complex, and combinations thereof,
the metal is selected from a rare-earth metal, a transition metal,
a late transition metal, and combinations thereof, and
the metal complex is selected from an alkali metal, an alkaline
earth metal, a rare-earth metal, a transition metal, a late
transition metal, and combinations thereof.
BRIEF DESCRIPTION OF THE DRAWINGS
These and/or other aspects will become apparent and more readily
appreciated from the following description of the embodiments,
taken in conjunction with the accompanying drawings in which:
FIG. 1 is a schematic cross-sectional view illustrating an organic
light-emitting device according to an embodiment;
FIG. 2 is a schematic cross-sectional view illustrating an organic
light-emitting device according to an embodiment;
FIG. 3 is a schematic cross-sectional view illustrating an organic
light-emitting device according to an embodiment;
FIG. 4 is a schematic cross-sectional view illustrating an organic
light-emitting device according to an embodiment;
FIG. 5 is a schematic cross-sectional view illustrating an organic
light-emitting device according to an embodiment; and
FIG. 6 is a schematic cross-sectional view illustrating an organic
light-emitting device according to an embodiment.
DETAILED DESCRIPTION
Reference will now be made in more detail to embodiments, examples
of which are illustrated in the accompanying drawings, wherein like
reference numerals refer to like elements throughout. In this
regard, the present embodiments may have different forms and should
not be construed as being limited to the descriptions set forth
herein. Accordingly, the embodiments are merely described below, by
referring to the drawings, to explain aspects of the present
description. As used herein, the term "and/or" includes any and all
combinations of one or more of the associated listed items.
Expressions such as "at least one of," "one of," and "selected
from," when preceding a list of elements, modify the entire list of
elements and do not modify the individual elements of the list.
Further, the use of "may" when describing embodiments of the
present invention refers to "one or more embodiments of the present
invention."
According to an embodiment of the present disclosure, an organic
light-emitting device may include a first electrode;
a second electrode facing the first electrode;
m emission units stacked between the first electrode and the second
electrode; and
m-1 charge generating layer(s) between each of the two adjacent
emission units from among the m emission units, the m-1 charge
generating layer(s) including m-1 n-type charge generating layer(s)
and m-1 p-type charge generating layer(s),
wherein m may be an integer of 2 or greater,
a maximum emission wavelength of light emitted from at least one of
the m emission units may differ from that of light emitted from at
least one of the other emission units,
at least one of the m-1 n-type charge generating layer(s) may
include a metal-containing material and an electron transporting
metal-non-containing material,
the metal-containing material may include a metal, a metal complex,
or a combination thereof,
the metal may include a rare-earth metal, a transition metal, a
late transition metal, or a combination thereof, and
the metal complex may include an alkali metal, an alkaline earth
metal, a rare-earth metal, a transition metal, a late transition
metal, or a combination thereof.
FIG. 1 illustrates a schematic view of an organic light-emitting
device 10 according to an embodiment of the present disclosure. As
shown in FIG. 1, an organic light-emitting device 10 according to
an embodiment may include a first electrode 110; a second electrode
190 facing the first electrode; m emission units 153 stacked
between the first electrode 110 and the second electrode 120; and
m-1 charge generating layer(s) 155 between each of the two adjacent
emission units 153 from among the m emission units 153, the m-1
charge generating layer(s) including m-1 n-type charge generating
layer(s) 155' and m-1 p-type charge generating layer(s) 155''
(e.g., each charge generating layer 155 may include an n-type
charge generating layer 155' and a p-type charge generating layer
155'').
The "emission unit" as used herein is not particularly limited and
may be any suitable emission unit capable of emission. In some
embodiments, the emission unit may include at least one emission
layer. In some embodiments, the emission unit may further include
an organic layer, in addition to an emission layer.
The organic light-emitting device 10 may include m stacked emission
units 153, wherein m may be an integer of 2 or greater. m, which
denotes the number of emission units, may be any suitable integer,
and the upper limit of the number of emission units is not
particularly limited. In some embodiments, the organic
light-emitting device may include 2, 3, 4, or 5 emission units.
A maximum emission wavelength of light emitted from at least one of
the m emission units may differ from that of light emitted from at
least one of the other emission units. In some embodiments, in an
organic light-emitting device that includes a first emission unit
and a second emission unit that are stacked together, the maximum
emission wavelength of light emitted from the first emission unit
may differ from that of light emitted from the second emission
unit. In this case, an emission layer of the first emission unit
and that of the second emission unit may each independently include
i) a single-layered structure including a single layer that
includes a single material, ii) a single-layered structure
including a single layer that includes a plurality of different
materials, or iii) a multi-layered structure having a plurality of
layers that include a plurality of different materials.
Accordingly, light emitted from the first emission unit or the
second emission unit may be single color light or mixed color
light. In some embodiments, in an organic light-emitting device
that includes a first emission unit, a second emission unit, and a
third emission unit that are stacked together, the maximum emission
wavelength of light emitted from the first emission unit may be the
same as that of light emitted from the second emission unit,
whereas the maximum emission wavelength of light emitted from the
third emission unit may differ from that of light emitted from the
first and second emission units. In some embodiments, the maximum
emission wavelength of light emitted from the first emission unit,
the maximum emission wavelength of light emitted from the second
emission unit, and the maximum emission wavelength of light emitted
from the third emission unit may differ from one another.
The organic light-emitting device 10 may include the charge
generating layer 155 between the two adjacent emission units 153
from among the m emission units 153. Here, the term "adjacent" as
used herein may refer to an arrangement of two layers positioned
closest to each other. In some embodiments, the term "two adjacent
emission units" may refer to an arrangement of two emission units
disposed closest to each other from among a plurality of emission
units. For example, the term "adjacent" may refer to an arrangement
of two layers that, in some embodiments, may physically contact
each other, and in other embodiments, may have another layer
disposed therebetween. In some embodiments, an emission unit
adjacent to a second electrode may refer to an emission unit
disposed closest to the second electrode from among a plurality of
emission units. In some embodiments, the second electrode may
physically contact the emission unit, or additional layers other
than the emission units may be present between the second electrode
and the emission unit. In some embodiments, an electron transport
layer may be between the second electrode and the emission unit. A
charge generating layer may be between two adjacent emission
units.
The charge generating layer may function as a cathode for one of
the two adjacent emission units by generating electrons and as an
anode for the other emission unit by generating holes. The charge
generating layer may separate adjacent emission units, while not
being directed connected to an electrode. In some embodiments, an
organic light-emitting device including m emission units may
include m-1 charge generating layer(s).
The charge generating layer 155 may include the n-type charge
generating layer 155' and the p-type charge generating layer 155''.
In some embodiments, the n-type charge generating layer 155' and
the p-type charge generating layer 155'' may directly contact each
other so as to form an NP junction (e.g., a P-N junction). Due to
the NP junction, electrons and holes may be concurrently or
simultaneously generated between the n-type charge generating layer
155' and the p-type charge generating layer 155''. The generated
electrons may be transferred to one emission unit of the two
adjacent emission units through the n-type charge generating layer
155'. The generated holes may be transferred to another emission
unit of the two adjacent emission units through the p-type charge
generating layer 155''. In addition, since the charge generating
layers 155 may each include one n-type charge generating layer 155'
and one p-type charge generating layer 155'', the organic
light-emitting device 10 that includes m-1 charge generating
layer(s) 155 may include m-1 n-type charge generating layer(s) 155'
and m-1 p-type charge generating layer(s) 155''.
The term "n-type" as used herein may refer to n-type semiconductor
properties, for example, properties capable of injection and
transport of electrons. The term "p-type" as used herein may refer
to p-type semiconductor properties, for example, properties capable
of injection and transport of holes.
At least one of the m-1 n-type charge generating layer(s) may
include a metal-containing material and an electron transporting
metal-non-containing material (e.g., electron transporting material
that does not include metal).
The metal-containing material may include a metal, a metal complex,
or a combination thereof.
According to an embodiment, when at least one of the m-1 n-type
charge generating layer(s) includes a metal as the metal-containing
material, the metal may include a rare-earth metal, a transition
metal, a late transition metal, or a combination thereof. In some
embodiments, when at least one of the m-1 n-type charge generating
layer(s) includes a metal as the metal-containing material, the
metal may be selected from lanthanum (La), cerium (Ce),
praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm),
europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy),
holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and
lutetium (Lu). According to an embodiment, when at least one of the
m-1 n-type charge generating layer(s) includes a metal as the
metal-containing material, the metal may be Yb, but embodiments are
not limited thereto.
In one or more embodiments, when at least one of the m-1 n-type
charge generating layer(s) includes a metal complex as the
metal-containing material, the metal complex may include an alkali
metal, an alkaline earth metal, a rare-earth metal, a transition
metal, a late transition metal, or a combination thereof. In some
embodiments, when at least one of the m-1 n-type charge generating
layer(s) includes a metal complex as the metal-containing material,
a metal of the metal complex may be selected from lithium (Li),
aluminum (Al), titanium (Ti), zirconium (Zr), hafnium (Hf), zinc
(Zn), and copper (Cu). According to an embodiment, when at least
one of the m-1 n-type charge generating layer(s) includes a metal
complex as the metal-containing material, the metal complex may be
a Li complex or an Al complex, but embodiments are not limited
thereto.
When at least one of the m-1 n-type charge generating layer(s)
includes a metal complex as the metal-containing material, the
metal complex may include at least one organic ligand selected from
a hydroxyquinoline, a hydroxyisoquinoline, a hydroxy
benzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a
hydroxyphenyl oxazole, a hydroxyphenyl thiazole, a hydroxydiphenyl
oxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl
pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenyl
benzothiazole, a bipyridine, a phenanthroline, and a
cyclopentadiene. In some embodiments, when at least one of the m-1
n-type charge generating layer(s) includes a metal complex as the
metal-containing material, the metal complex may include at least
one selected from a substituted or unsubstituted hydroxyquinoline
and a substituted or unsubstituted hydroxyphenyl benzothiazole, but
embodiments are not limited thereto.
In some embodiments, when at least one of the m-1 n-type charge
generating layer(s) includes a metal complex as the
metal-containing material, the metal complex may be a lithium
quinolate (Liq) and/or an aluminum quinolate (Alq.sub.3).
In some embodiments, a lowest unoccupied molecular orbital (LUMO)
energy level of the electron transporting metal-non-containing
material may be about -4.0 electron volts (eV) or greater. In some
embodiments, a LUMO energy level of the electron transporting
metal-non-containing material may be about -3.8 eV or greater. In
some embodiments, a LUMO energy level of the electron transporting
metal-non-containing material may be about -3.5 eV or greater.
Since an organic compound having a LUMO energy level of about -4.0
eV or greater has a slight difference in LUMO energy level with
peripheral layers, the organic compound may efficiently (or
suitably) transfer electrons generated in the n-type charge
generating layer to the peripheral layers.
In one or more embodiments, the electron transporting
metal-non-containing material may be an organic compound including
at least one .pi. electron-depleted nitrogen-containing ring.
The term ".pi. electron-depleted nitrogen-containing ring" as used
herein may refer to a C.sub.1-C.sub.60 heterocyclic group having at
least one *--N.dbd.*' moiety as a ring-forming moiety.
For example, the ".pi. electron-depleted nitrogen-containing ring"
may be i) a 5-membered to 7-membered heteromonocyclic group having
at least one *--N.dbd.*' moiety, ii) a heteropolycyclic group in
which two or more 5-membered to 7-membered heteromonocyclic groups
each having at least one *--N.dbd.*' moiety are condensed (e.g.,
fused), and/or iii) a heteropolycyclic group in which at least one
5-membered to 7-membered heteromonocyclic group having at least one
*--N.dbd.*' moiety is condensed with at least one C.sub.5-C.sub.60
carbocyclic group.
In some embodiments, the electron transporting metal-non-containing
material may be an organic compound including at least one selected
from an imidazole ring, a pyrazole ring, a thiazole ring, an
isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine
ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an
indazole ring, a purine ring, a quinoline ring, an isoquinoline
ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine
ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a
phenanthridine ring, an acridine ring, a phenanthroline ring, a
phenazine ring, a benzoimidazole ring, an iso-benzothiazole ring, a
benzoxazole ring, an isobenzoxazole ring, a triazole ring, a
tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole
ring, an imidazopyridine ring, an imidazopyrimidine ring, and
indenoquinoline ring. In some embodiments, the electron
transporting metal-non-containing material may be an organic
compound including at least one selected from a phenanthroline
ring, an imidazole ring, a pyridine ring, a pyrazine ring, a
pyrimidine ring, a pyridazine ring, and a triazine ring.
According to an embodiment, the electron transporting
metal-non-containing material may be represented by Formula 1:
[Ar.sub.1].sub.c1-[(L.sub.1).sub.a1-R.sub.1].sub.b1, Formula 1
wherein, in Formula 1,
Ar.sub.1 may be a substituted or unsubstituted C.sub.5-C.sub.60
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.60 heterocyclic group,
c1 may be 1, 2, or 3,
when c1 is 2 or greater, a plurality of Ar.sub.1(s) may be
identical to or different from each other, and the plurality of
Ar.sub.1(s) may be connected to a respective one another via a
single bond,
L.sub.1 may be selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenylene group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroarylene group, a substituted or
unsubstituted divalent non-aromatic condensed polycyclic group, and
a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group,
a1 may be an integer selected from 0 to 5,
when a1 is 0, *-(L.sub.1).sub.a1-*' may be a single bond, and when
a1 is 2 or greater, a plurality of L.sub.1(s) may be identical to
or different from each other,
R.sub.1 may be selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
wherein Q.sub.1 to Q.sub.3 may be each independently a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, or a naphthyl
group,
b1 may be an integer selected from 1 to 5, and
when b1 is 2 or greater, a plurality of
[(L.sub.1).sub.a1-R.sub.1](s) may be identical to or different from
each other.
In some embodiments, in Formula 1,
Ar.sub.1 may be selected from the group consisting of:
a benzene group, a naphthalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, a naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, a
dibenzofuran group, a dibenzothiophene group, a carbazole group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, an indazole
group, a purine group, a quinoline group, an isoquinoline group, a
benzoquinoline group, a phthalazine group, a naphthyridine group, a
quinoxaline group, a quinazoline group, a cinnoline group, a
phenanthridine group, an acridine group, a phenanthroline group, a
phenazine group, a benzoimidazole group, an iso-benzothiazole
group, a benzoxazole group, an isobenzoxazole group, a triazole
group, a tetrazole group, an oxadiazole group, a triazine group, a
thiadiazole group, an imidazopyridine group, an imidazopyrimidine
group, indenoquinoline group, a pyridoquinazoline group, and a
benzoimidazoquinazoline group; and
a benzene group, a naphthalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, a naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, a
dibenzofuran group, a dibenzothiophene group, a carbazole group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, an indazole
group, a purine group, a quinoline group, an isoquinoline group, a
benzoquinoline group, a phthalazine group, a naphthyridine group, a
quinoxaline group, a quinazoline group, a cinnoline group, a
phenanthridine group, an acridine group, a phenanthroline group, a
phenazine group, a benzoimidazole group, an iso-benzothiazole
group, a benzoxazole group, an isobenzoxazole group, a triazole
group, a tetrazole group, an oxadiazole group, a triazine group, a
thiadiazole group, an imidazopyridine group, an imidazopyrimidine
group, indenoquinoline group, a pyridoquinazoline group, and a
benzoimidazoquinazoline group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
L.sub.1 may be selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group, and
R.sub.1 may be selected from the group consisting of:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, an
azacarbazolyl group, and a pyridonaphthyridinyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, an
azacarbazolyl group, and a pyridonaphthyridinyl group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group; and
--S(.dbd.O).sub.2(Q.sub.1) and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
wherein Q.sub.1, Q.sub.2, and Q.sub.31 to Q.sub.33 may be each
independently a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
or a naphthyl group.
According to an embodiment, the electron transporting
metal-non-containing material may be selected from Compounds 1 to
21, but embodiments are not limited thereto:
##STR00001## ##STR00002## ##STR00003## ##STR00004##
##STR00005##
According to an embodiment, when an n-type charge generating layer,
which includes the metal-containing material and the electron
transporting metal-non-containing material, includes the metal as
the metal-containing material, a weight ratio of the metal to the
electron transporting metal-non-containing material may be in a
range of about 0.01:100 to about 15:100. In some embodiments, a
weight ratio of the metal to the electron transporting
metal-non-containing material may be in a range of about 1:100 to
about 5:100, but embodiments are not limited thereto.
According to an embodiment, when an n-type charge generating layer,
which includes the metal-containing material and the electron
transporting metal-non-containing material, includes the metal
complex as the metal-containing material, a weight ratio of the
metal complex to the electron transporting metal-non-containing
material may be in a range of about 1:100 to about 100:1. In some
embodiments, a weight ratio of the metal complex to the electron
transporting metal-non-containing material may be in a range of
about 1:50 to about 50:1. In some embodiments, a weight ratio of
the metal complex to the electron transporting metal-non-containing
material may be in a range of about 1:25 to about 25:1. In some
embodiments, a weight ratio of the metal complex to the electron
transporting metal-non-containing material may be in a range of
about 3:7 to about 7:3, but embodiments are not limited
thereto.
The p-type charge generating layer may substantially smoothly
generate holes between the p-type charge generating layer and the
n-type charge generating layer, and a material for the p-type
charge generating layer is not particularly limited, and may be any
suitable material capable of smoothly transferring generated holes
to an adjacent emission unit. In some embodiments, the p-type
charge generating layer may include only an organic compound. In
some embodiments, the p-type charge generating layer may further
include a metal oxide. In some embodiments, the p-type charge
generating layer may further include a p-type dopant.
According to an embodiment, the p-type charge generating layer may
include at least one selected from a quinone derivative, a metal
oxide, and a cyano group-containing compound, but embodiments are
not limited thereto.
In some embodiments, a material for the p-type charge generating
layer may include at least one selected from the group consisting
of:
a quinone derivative, such as tetracyanoquinodimethane (TCNQ)
and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane
(F4-TCNQ);
a metal oxide, such as tungsten oxide and/or molybdenum oxide;
1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
compounds represented by Formula 221, but embodiments are not
limited thereto:
##STR00006##
wherein, in Formula 221,
R.sub.221 to R.sub.223 may be each independently selected from a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl
group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenyl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted
monovalent non-aromatic condensed polycyclic group, and a
substituted or unsubstituted monovalent non-aromatic condensed
heteropolycyclic group, provided that at least one selected from
R.sub.221 to R.sub.223 may include at least one substituent
selected from a cyano group, --F, --Cl, --Br, --I, a
C.sub.1-C.sub.20 alkyl group substituted with --F, a
C.sub.1-C.sub.20 alkyl group substituted with --Cl, a
C.sub.1-C.sub.20 alkyl group substituted with --Br, and a
C.sub.1-C.sub.20 alkyl group substituted with --I.
According to an embodiment, the thickness of the n-type charge
generating layer and that of the p-type charge generating layer may
be each independently in a range of about 20 .ANG. to about 1,000
.ANG.. According to an embodiment, the thickness of the n-type
charge generating layer and that of the p-type charge generating
layer may be each independently in a range of about 50 .ANG. to
about 500 .ANG.. According to an embodiment, the thickness of the
n-type charge generating layer may be in a range of about 100 .ANG.
to about 300 .ANG., and the thickness of the p-type charge
generating layer may be in a range of about 50 .ANG. to about 200
.ANG., but embodiments are not limited thereto.
According to an embodiment, the organic light-emitting device 10
may further include a hole transport region between the first
electrode and an emission unit adjacent to the first electrode from
among the m emission units, wherein the hole transport region may
include a p-dopant having a LUMO energy level of about -3.5 eV or
less. The p-dopant may include at least one selected from a quinone
derivative, a metal oxide, and a cyano group-containing compound,
but embodiments are not limited thereto. In some embodiments, the
p-dopant may include at least one selected from the group
consisting of:
a quinone derivative, such as tetracyanoquinodimethane (TCNQ)
and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane
(F4-TCNQ);
a metal oxide, such as tungsten oxide and/or molybdenum oxide;
1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
compounds represented by Formula 221, but is not limited
thereto.
FIG. 2 illustrates a schematic view of an organic light-emitting
device 11 according to an embodiment. According to an embodiment,
as shown in FIG. 2, the organic light-emitting device 11 may
further include an electron transport layer 157 between the
emission unit 153 adjacent to the second electrode 190 from among
the m emission units 153 and the second electrode 190.
The electron transport layer 157 may include a metal-containing
material and an electron transporting metal-non-containing material
(e.g., an electron transporting material that does not include
metal).
The metal-containing material may include a metal, a metal complex,
or a combination thereof.
In some embodiments, when the electron transport layer includes a
metal as the metal-containing material, the metal may include an
alkali metal, an alkaline earth metal, a rare-earth metal, a
transition metal, a late transition metal, or a combination
thereof. In some embodiments, when the electron transport layer
includes a metal as the metal-containing material, the metal may be
selected from lithium (Li), sodium (Na), potassium (K), rubidium
(Rb), cesium (Cs), francium (Fr), beryllium (Be), magnesium (Mg),
calcium (Ca), strontium (Sr), barium (Ba), radium (Ra), La, Ce, Pr,
Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb and Lu. According to an
embodiment, when the electron transport layer includes a metal as
the metal-containing material, the metal may be selected from Li,
Mg, and Yb, but embodiments are not limited thereto.
In some embodiments, when the electron transport layer includes a
metal complex as the metal-containing material, the metal complex
may include an alkali metal, an alkaline earth metal, a rare-earth
metal, a transition metal, a late transition metal, or a
combination thereof. In some embodiments, when the electron
transport layer includes a metal complex as the metal-containing
material, the metal complex may include Li, Al, Ti, Zr, Hf, Zn,
and/or Cu. According to an embodiment, when the electron transport
layer includes a metal complex as the metal-containing material,
the metal complex may be a Li complex or an Al complex, but
embodiments are not limited thereto.
When the electron transport layer includes a metal complex as the
metal-containing material, the metal complex may further include at
least one organic ligand selected from a hydroxyquinoline, a
hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a
hydroxyphenanthridine, a hydroxyphenyl oxazole, a hydroxyphenyl
thiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl
thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl
benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a
phenanthroline, and a cyclopentadiene. In some embodiments, when
the electron transport layer includes a metal complex as the
metal-containing material, the metal complex may include at least
one selected from a substituted or unsubstituted hydroxyquinoline
and a substituted or unsubstituted hydroxyphenylbenzothiazole.
In some embodiments, when the electron transport layer includes a
metal complex as the metal-containing material, the metal complex
may be a lithium quinolate (Liq) and/or an aluminum quinolate
(Alq.sub.3).
The electron transporting metal-non-containing material included in
the electron transport layer may be an organic compound including
at least one .pi. electron-depleted nitrogen-containing ring. In
some embodiments, the electron transporting metal-non-containing
material may be an organic compound including at least one selected
from an imidazole ring, a pyrazole ring, a thiazole ring, an
isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine
ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an
indazole ring, a purine ring, a quinoline ring, an isoquinoline
ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine
ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a
phenanthridine ring, an acridine ring, a phenanthroline ring, a
phenazine ring, a benzoimidazole ring, an iso-benzothiazole ring, a
benzoxazole ring, an isobenzoxazole ring, a triazole ring, a
tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole
ring, an imidazopyridine ring, an imidazopyrimidine ring, and
indenoquinoline ring. In some embodiments, the electron
transporting metal-non-containing material may be an organic
compound including at least one selected from a phenanthroline
ring, an imidazole ring, a pyridine ring, a pyrazine ring, a
pyrimidine ring, a pyridazine ring, and a triazine ring. In some
embodiments, the electron transporting metal-non-containing
material may be selected from Compounds 1 to 6 (as illustrated
above).
In some embodiments, the metal-containing material and the electron
transporting metal-non-containing material included in at least one
of the m-1 n-type charge generating layer(s) may be the same as the
metal-containing material and the electron transporting
metal-non-containing material included in the electron transport
layer, respectively. In some embodiments, at least one of the m-1
n-type charge generating layer(s) may include Yb as the
metal-containing material and Compound 1 as the electron
transporting metal-non-containing material. The electron transport
layer may include Yb as the metal-containing material and Compound
1 as the electron transporting metal-non-containing material.
According to some embodiments, the metal-containing material
included in at least one of the m-1 n-type charge generating
layer(s) may differ from the metal-containing material included in
the electron transport layer; the electron transporting
metal-non-containing material included in at least one of the m-1
n-type charge generating layer(s) may differ from the electron
transporting metal-non-containing material included in the electron
transport layer; or the metal-containing material included in at
least one of the m-1 n-type charge generating layer(s) may differ
from the metal-containing material included in the electron
transport layer, and the electron transporting metal-non-containing
material included in at least one of the m-1 n-type charge
generating layer(s) may differ from the electron transporting
metal-non-containing material included in the electron transport
layer.
In some embodiments, at least one of the m-1 n-type charge
generating layer(s) may include Yb as the metal-containing material
and Compound 1 as the electron transporting metal-non-containing
material. The electron transport layer may include Li as the
metal-containing material and Compound 1 as the electron
transporting metal-non-containing material. In some embodiments, at
least one of the m-1 n-type charge generating layer(s) may include
Yb as the metal-containing material and Compound 1 as the electron
transporting metal-non-containing material. The electron transport
layer may include Liq as the metal-containing material and Compound
5 as the electron transporting metal-non-containing material.
According to some embodiments, m may be 3 or greater, and the m-1
n-type charge generating layers may all include the same
metal-containing material and the same electron transporting
metal-non-containing material, and
the metal-containing material included in the m-1 n-type charge
generating layers may differ from the metal-containing material
included in the electron transport layer; the electron transporting
metal-non-containing material included in the m-1 n-type charge
generating layers may differ from the electron transporting
metal-non-containing material included in the electron transport
layer; or the metal-containing material included in the m-1 n-type
charge generating layers may differ from the metal-containing
material included in the electron transport layer, and the electron
transporting metal-non-containing material included in the m-1
n-type charge generating layers may differ from the electron
transporting metal-non-containing material included in the electron
transport layer.
According to an embodiment, the organic light-emitting device 11
may further include, in addition to an electron transport layer
between the second electrode and an emission unit adjacent to the
second electrode from among the m emission units, a hole transport
region between the first electrode and an emission unit adjacent to
the first electrode from among the m emission units, wherein the
hole transport region may include a p-dopant having a LUMO energy
level of about -3.5 eV or less. The p-dopant may be the same as
described herein.
In an organic light-emitting device according to an embodiment, m
may be 2. That is, in some embodiments, the organic light-emitting
device may include only two emission units. In some embodiments, an
organic light-emitting device may include a first electrode, a
first emission unit, a first charge generating layer, a second
emission unit, and a second electrode, which are stacked in this
stated order. The organic light-emitting device may further include
an electron transport layer between the second emission unit and
the second electrode.
In an organic light-emitting device according to another
embodiment, m may be 3. That is, in some embodiments, the organic
light-emitting device may include only three emission units. In
some embodiments, an organic light-emitting device may include a
first electrode, a first emission unit, a first charge generating
layer, a second emission unit, a second charge generating layer, a
third emission unit, and a second electrode, which are stacked in
this stated order. The organic light-emitting device may further
include an electron transport layer between the third emission unit
and the second electrode.
According to another embodiment, an organic light-emitting device
may include a first electrode;
a second electrode facing the first electrode;
m emission units stacked between the first electrode and the second
electrode; and
m-1 charge generating layer(s) between the two adjacent emission
units from among the m emission units, m-1 charge generating
layer(s) including m-1 n-type charge generating layer(s) and m-1
p-type charge generating layer(s),
wherein m may be an integer of 2 or greater,
a maximum emission wavelength of light emitted from at least one of
the m emission units may differ from that of light emitted from at
least one of the other emission units,
at least one of the m-1 n-type charge generating layer(s) may
include a metal-containing material and an electron transporting
metal-non-containing material,
the metal-containing material may include a metal, a metal complex,
or a combination thereof,
the metal may include a rare-earth metal, a transition metal, a
late transition metal, or a combination thereof, and
the metal complex may include an alkali metal, an alkaline earth
metal, a rare-earth metal, a transition metal, a late transition
metal, or a combination thereof.
The organic light-emitting device may further include an electron
transport layer between the second electrode and an emission unit
adjacent to the second electrode from among the m emission
units,
wherein the electron transport layer may include a metal-containing
material and an electron transporting metal-non-containing
material,
the metal-containing material may include a metal, a metal complex,
or a combination thereof,
the metal may include an alkali metal, an alkaline earth metal, a
rare-earth metal, a transition metal, a late transition metal, or a
combination thereof, and
the metal complex may include an alkali metal, an alkaline earth
metal, a rare-earth metal, a transition metal, a late transition
metal, or a combination thereof.
According to another embodiment, an organic light-emitting device
may include a first electrode;
a second electrode facing the first electrode;
m emission units stacked between the first electrode and the second
electrode; and
m-1 charge generating layer(s) between two adjacent emission units
from among the m emission units and including m-1 n-type charge
generating layer(s) and m-1 p-type charge generating layer(s),
wherein m may be an integer of 2 or greater,
a maximum emission wavelength of light emitted from at least one of
the m emission units may differ from that of light emitted from at
least one of the other emission units,
at least one of the m-1 n-type charge generating layer(s) may
include a metal-containing material and an electron transporting
metal-non-containing material,
the metal-containing material may include a metal, a metal complex,
or a combination thereof,
the metal may include a rare-earth metal, a transition metal, a
late transition metal, or a combination thereof, and
the metal complex may include an alkali metal, an alkaline earth
metal, a rare-earth metal, a transition metal, a late transition
metal, or a combination thereof.
The organic light-emitting device may further include an electron
transport layer between the second electrode and an emission unit
adjacent to the second electrode from among the m emission
units,
wherein the electron transport layer may include a metal-containing
material and an electron transporting metal-non-containing
material,
the metal-containing material may include a metal, a metal complex,
or a combination thereof,
the metal may include an alkali metal, an alkaline earth metal, a
rare-earth metal, a transition metal, a late transition metal, or a
combination thereof, and
the metal complex may include an alkali metal, an alkaline earth
metal, a rare-earth metal, a transition metal, a late transition
metal, or a combination thereof.
When the n-type charge generating layer includes a metal-containing
material and an electron transporting metal-non-containing
material, wherein the metal-containing material is a metal
including a rare-earth metal, a transition metal, a late transition
metal, or a combination thereof, the metal may have relatively
great atomic weight or size compared to an alkali metal, and thus
may exhibit no or reduced intermixing with peripheral layers.
Accordingly, an organic light-emitting device including the n-type
charge generating layer according to embodiments of the present
disclosure may have long lifespan and/or improved stability.
In addition, when the n-type charge generating layer includes a
metal-containing material and an electron transporting
metal-non-containing material, wherein the metal-containing
material is a metal complex, the metal in the metal complex may be
stabilized by a ligand (e.g., an organic ligand included in the
metal complex). Accordingly, an organic light-emitting device
including the n-type charge generating layer according to
embodiments of the present disclosure may have improved stability
due to interaction between the metal complex and the electron
transporting metal-non-containing material.
In addition, when the n-type charge generating layer includes a
metal-containing material and an electron transporting
metal-non-containing material, wherein the metal-containing
material includes both a metal of a rare-earth metal, a transition
metal, a late transition metal, or a combination thereof and a
metal complex, an organic light-emitting device including the
n-type charge generating layer may have both of the foregoing
advantages.
Description of FIG. 3
FIG. 3 is a schematic cross-sectional view illustrating an organic
light-emitting device 12 according to an embodiment. The organic
light-emitting device 12 may include the first electrode 110, the
organic layer 150, and the second electrode 190.
Hereinafter, the structure of the organic light-emitting device 12
according to an embodiment and a method of manufacturing an organic
light-emitting device according to an embodiment will be described
in connection with FIG. 3.
First Electrode 110
In FIG. 3, a substrate may be additionally disposed under the first
electrode 110 or above the second electrode 190. The substrate may
be a glass substrate or a plastic substrate, each having excellent
mechanical strength, thermal stability, transparency, surface
smoothness, ease of handling, and/or water-resistance.
The first electrode 110 may be formed by depositing or sputtering a
material for the first electrode 110 on the substrate. When the
first electrode 110 is an anode, a material for the first electrode
110 may be selected from materials with a high work function to
facilitate hole injection.
The first electrode 110 may be a reflective electrode, a
semi-transmissive electrode, or a transmissive electrode. When the
first electrode 110 is a transmissive electrode, a material for the
first electrode 110 may be selected from indium tin oxide (ITO),
indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide (ZnO),
and any combinations thereof, but is not limited thereto. In one or
more embodiments, when the first electrode 110 is a
semi-transmissive electrode or a reflective electrode, a material
for the first electrode 110 may be selected from magnesium (Mg),
silver (Ag), aluminum (Al), aluminum-lithium (Al--Li), calcium
(Ca), magnesium-indium (Mg--In), magnesium-silver (Mg--Ag), and any
combinations thereof, but is not limited thereto.
The first electrode 110 may have a single-layered structure, or a
multi-layered structure including two or more layers. For example,
the first electrode 110 may have a three-layered structure of
ITO/Ag/ITO, but the structure of the first electrode 110 is not
limited thereto.
Organic Layer 150
The organic layer 150 may be positioned on the first electrode 110.
The organic layer 150 may include an emission unit.
The organic layer 150 may further include a hole transport region
between the first electrode 110 and the emission unit and an
electron transport region between the emission unit and the second
electrode 190.
Hole Transport Region in Organic Layer 150
The hole transport region may have i) a single-layered structure
including a single layer including a single material, ii) a
single-layered structure including a single layer including a
plurality of different materials, or iii) a multi-layered structure
having a plurality of layers including a plurality of different
materials.
The hole transport region may include at least one layer selected
from a hole injection layer, a hole transport layer, an emission
auxiliary layer, and an electron blocking layer.
For example, the hole transport region may have a single-layered
structure including a single layer including a plurality of
different materials, or a multi-layered structure of hole injection
layer/hole transport layer, hole injection layer/hole transport
layer/emission auxiliary layer, hole injection layer/emission
auxiliary layer, hole transport layer/emission auxiliary layer, or
hole injection layer/hole transport layer/electron blocking layer,
wherein for each structure, constituting layers are sequentially
stacked from the first electrode 110 in this stated order, but the
structure of the hole transport region is not limited thereto.
The hole transport region may include at least one selected from
m-MTDATA, TDATA, 2-TNATA, NPB (NPD), .beta.-NPB, TPD, Spiro-TPD,
Spiro-NPB, methylated NPB, TAPC, HMTPD,
4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA),
polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),
poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)
(PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA),
polyaniline/poly(4-styrenesulfonate) (Pani/PSS), a compound
represented by Formula 201, and a compound represented by Formula
202:
##STR00007## ##STR00008## ##STR00009##
wherein, in Formulae 201 and 202,
L.sub.201 to L.sub.204 may be each independently selected from a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group,
a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene
group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkenylene group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroarylene group, a substituted
or unsubstituted divalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group,
L.sub.205 may be selected from *--O--*', *--S--',
*--N(Q.sub.201)-*', a substituted or unsubstituted C.sub.1-C.sub.20
alkylene group, a substituted or unsubstituted C.sub.2-C.sub.20
alkenylene group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkylene group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkylene group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted
or unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
a substituted or unsubstituted divalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted divalent
non-aromatic condensed heteropolycyclic group,
xa1 to xa4 may be each independently an integer selected from 0 to
3,
xa5 may be an integer selected from 1 to 10, and
R.sub.201 to R.sub.204 and Q.sub.201 may be each independently
selected from a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted monovalent non-aromatic
condensed heteropolycyclic group.
In some embodiments, in Formula 202, R.sub.201 and R.sub.202 may
optionally be bound to each other via a single bond, a
dimethyl-methylene group, or a diphenyl-methylene group, and
R.sub.203 and R.sub.204 may optionally be bound to each other via a
single bond, a dimethyl-methylene group, or a diphenyl-methylene
group.
In some embodiments, in Formulae 201 and 202,
L.sub.201 to L.sub.205 may be each independently selected from the
group consisting of:
a phenylene group, a pentalenylene group, an indenylene group, a
naphthylene group, an azulenylene group, a heptalenylene group, an
indacenylene group, an acenaphthylene group, a fluorenylene group,
a spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenalenylene group, a
phenanthrenylene group, an anthracenylene group, a fluoranthenylene
group, a triphenylenylene group, a pyrenylene group, a chrysenylene
group, a naphthacenylene group, a picenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a rubicenylene group, a coronenylene group, an
ovalenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group; and
a phenylene group, a pentalenylene group, an indenylene group, a
naphthylene group, an azulenylene group, a heptalenylene group, an
indacenylene group, an acenaphthylene group, a fluorenylene group,
a spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenalenylene group, a
phenanthrenylene group, an anthracenylene group, a fluoranthenylene
group, a triphenylenylene group, a pyrenylene group, a chrysenylene
group, a naphthacenylene group, a picenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a rubicenylene group, a coronenylene group, an
ovalenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group,
a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl
group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl
group, a phenyl group, a biphenyl group, a terphenyl group, a
phenyl group substituted with a C.sub.1-C.sub.10 alkyl group, a
phenyl group substituted with --F, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a phenalenyl group, a phenanthrenyl group, an anthracenyl
group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl
group, a chrysenyl group, a naphthacenyl group, a picenyl group, a
perylenyl group, a pentaphenyl group, a hexacenyl group, a
pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl
group, a thiophenyl group, a furanyl group, a carbazolyl group, an
indolyl group, an isoindolyl group, a benzofuranyl group, a
benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
dibenzosilolyl group, a pyridinyl group,
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33), and
--N(Q.sub.31)(Q.sub.32),
wherein Q.sub.31 to Q.sub.33 may each be independently selected
from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, and a
naphthyl group.
In one or more embodiments, xa1 to xa4 may be each independently 0,
1, or 2.
According to an embodiment, xa5 may be 1, 2, 3, or 4.
According to some embodiments, R.sub.201 to R.sub.204 and Q.sub.201
may be each independently selected from the group consisting
of:
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl
group, an indenyl group, a naphthyl group, an azulenyl group, a
heptalenyl group, an indacenyl group, an acenaphthyl group, a
fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group,
a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a
picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl
group, a pentacenyl group, a rubicenyl group, a coronenyl group, an
ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl
group, an indolyl group, an isoindolyl group, a benzofuranyl group,
a benzothiophenyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl
group; and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl
group, an indenyl group, a naphthyl group, an azulenyl group, a
heptalenyl group, an indacenyl group, an acenaphthyl group, a
fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group,
a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a
picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl
group, a pentacenyl group, a rubicenyl group, a coronenyl group, an
ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl
group, an indolyl group, an isoindolyl group, a benzofuranyl group,
a benzothiophenyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro
group, an amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclopentenyl group, a cyclohexenyl group, a phenyl group, a
biphenyl group, a terphenyl group, a phenyl group substituted with
a C.sub.1-C.sub.10 alkyl group, a phenyl group substituted with
--F, a pentalenyl group, an indenyl group, a naphthyl group, an
azulenyl group, a heptalenyl group, an indacenyl group, an
acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl
group, a furanyl group, a carbazolyl group, an indolyl group, an
isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a
dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl
group, a dibenzocarbazolyl group, a dibenzosilolyl group, a
pyridinyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), and
--N(Q.sub.31)(Q.sub.32),
wherein Q.sub.31 to Q.sub.33 may be the same as described
herein.
According to some embodiments, at least one selected from R.sub.201
to R.sub.203 in Formula 201 may be selected from the group
consisting of:
a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a
dibenzofuranyl group, and a dibenzothiophenyl group; and
a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a
dibenzofuranyl group, and a dibenzothiophenyl group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclopentenyl group, a cyclohexenyl group, a phenyl group, a
biphenyl group, a terphenyl group, a phenyl group substituted with
a C.sub.1-C.sub.10 alkyl group, a phenyl group substituted with
--F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl
group, a carbazolyl group, a dibenzofuranyl group, and a
dibenzothiophenyl group,
but embodiments are not limited thereto.
According to some embodiments, in Formula 202, i) R.sub.201 and
R.sub.202 may be bound to each other via a single bond, and/or ii)
R.sub.203 and R.sub.204 may be bound to each other via a single
bond.
According to some embodiments, at least one selected from R.sub.201
to R.sub.204 in Formula 202 may be selected from the group
consisting of:
a carbazolyl group; and
a carbazolyl group substituted with at least one selected from
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy
group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a phenyl group substituted
with a C.sub.1-C.sub.10 alkyl group, a phenyl group substituted
with --F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl
group, a carbazolyl group, a dibenzofuranyl group, and a
dibenzothiophenyl group, but embodiments are not limited
thereto.
The compound represented by Formula 201 may be represented by
Formula 201A:
##STR00010##
In some embodiments, the compound represented by Formula 201 may be
represented by Formula 201A(1), but embodiments are not limited
thereto:
##STR00011##
In some embodiments, the compound represented by Formula 201 may be
represented by Formula 201A-1, but embodiments are not limited
thereto:
##STR00012##
In some embodiments, the compound represented by Formula 202 may be
represented by Formula 202A, but embodiments are not limited
thereto:
##STR00013##
In some embodiments, the compound represented by Formula 202 may be
represented by Formula 202A-1:
##STR00014##
In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,
descriptions of L.sub.201 to L.sub.203, xa1 to xa3, xa5, and
R.sub.202 to R.sub.204 may each independently be the same as
descriptions thereof provided herein,
descriptions of R.sub.211 and R.sub.212 may each independently be
the same as the description provided herein in connection with
R.sub.203, and
R.sub.213 to R.sub.217 may be each independently selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a cyclopentyl group, a cyclohexyl group, a
cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a
phenyl group, a biphenyl group, a terphenyl group, a phenyl group
substituted with a C.sub.1-C.sub.10 alkyl group, a phenyl group
substituted with --F, a pentalenyl group, an indenyl group, a
naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl
group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl
group, a benzofluorenyl group, a dibenzofluorenyl group, a
phenalenyl group, a phenanthrenyl group, an anthracenyl group, a
fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a
chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl
group, a pentaphenyl group, a hexacenyl group, a pentacenyl group,
a rubicenyl group, a coronenyl group, an ovalenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, and a pyridinyl group.
For example, the hole transport region may include at least one
compound selected from Compounds HT1 to HT39, but embodiments are
not limited thereto:
##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019##
##STR00020## ##STR00021##
The thickness of the hole transport region may be in a range of
about 100 .ANG. to about 10,000 .ANG., for example, about 100 .ANG.
to about 1,000 .ANG.. When the hole transport region includes at
least one selected from a hole injection layer and a hole transport
layer, the thickness of the hole injection layer may be in a range
of about 100 .ANG. to about 9,000 .ANG., and in some embodiments,
about 100 .ANG. to about 1,000 .ANG.; the thickness of the hole
transport layer may be in a range of about 50 .ANG. to about 2,000
.ANG., and in some embodiments, about 100 .ANG. to about 1,500
.ANG.. When the thicknesses of the hole transport region, the hole
injection layer and the hole transport layer are within any of
these ranges, satisfactory (or suitable) hole transporting
characteristics may be obtained without a substantial increase in
driving voltage.
The emission auxiliary layer may increase the light-emission
efficiency by compensating for an optical resonance distance
according to the wavelength of light emitted by an emission layer,
and the electron blocking layer may block or reduce the flow of
electrons from an electron transport region. The emission auxiliary
layer and the electron blocking layer may each independently
include any of the materials as described above.
p-Dopant
The hole transport region may further include, in addition to the
materials described above, a charge-generation material for the
improvement of conductive properties. The charge-generation
material may be homogeneously or non-homogeneously dispersed in the
hole transport region.
The charge-generation material may be, for example, a p-dopant.
In one embodiment, the p-dopant may have a lowest unoccupied
molecular orbital (LUMO) of -3.5 eV or less.
The p-dopant may include at least one selected from a quinone
derivative, a metal oxide, and a cyano group-containing compound,
but embodiments are not limited thereto.
In some embodiments, the p-dopant may include at least one selected
from the group consisting of:
a quinone derivative, such as tetracyanoquinodimethane (TCNQ)
and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane
(F4-TCNQ);
a metal oxide, such as tungsten oxide and/or molybdenum oxide;
1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
compounds represented by Formula 221, but embodiments are not
limited thereto:
##STR00022##
wherein, in Formula 221,
R.sub.221 to R.sub.223 may be each independently selected from a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl
group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenyl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted
monovalent non-aromatic condensed polycyclic group, and a
substituted or unsubstituted monovalent non-aromatic condensed
heteropolycyclic group, provided that at least one selected from
R.sub.221 to R.sub.223 may include at least one substituent
selected from a cyano group, --F, --Cl, --Br, --I, a
C.sub.1-C.sub.20 alkyl group substituted with --F, a
C.sub.1-C.sub.20 alkyl group substituted with --Cl, a
C.sub.1-C.sub.20 alkyl group substituted with --Br, and a
C.sub.1-C.sub.20 alkyl group substituted with --I.
Emission Layer in Organic Layer 150
In the organic light-emitting device 12, an emission unit may
include an emission layer, wherein the emission layer may have a
stacked structure of two or more layers selected from a red
emission layer, a green emission layer, a yellow emission layer,
and a blue emission layer, in which the two or more layers may
contact each other or may be separated from each other. In one or
more embodiments, the emission layer may include two or more
materials selected from a red-light emission material, a
green-light emission material, a yellow-light emission material,
and a blue-light emission material, in which the two or more
materials may be mixed together in a single layer.
The emission unit may further include an upper auxiliary layer
formed on the emission layer and/or a lower auxiliary layer formed
below (e.g., under) the emission layer. The lower auxiliary layer
may perform substantially the same functions as the above-described
hole transport layer, emission auxiliary layer, and electron
blocking layer; and the upper auxiliary layer may perform
substantially the same functions as the below-described buffer
layer, hole blocking layer, electron control layer, and electron
transport layer. The materials for the lower auxiliary layer and
the upper auxiliary layer may be the same as those described herein
in connection with the materials for the hole transport region and
the electron transport region.
The emission layer may include a host and a dopant. The dopant may
include at least one selected from a phosphorescent dopant and a
fluorescent dopant.
The amount of the dopant in the emission layer may be in a range of
about 0.01 to about 15 parts by weight based on 100 parts by weight
of the host, but is not limited thereto.
The thickness of the emission layer may be in a range of about 100
.ANG. to about 1,000 .ANG., in some embodiments, about 200 .ANG. to
about 600 .ANG.. When the thickness of the emission layer is within
any of these ranges, excellent (or suitable) light-emission
characteristics may be obtained without a substantial increase in
driving voltage.
Host in Emission Layer
The host may include a compound represented by Formula 301:
[Ar.sub.301].sub.xb11-[(L.sub.301).sub.xb1-R.sub.301].sub.xb21,
Formula 301
wherein, in Formula 301,
Ar.sub.301 may be a substituted or unsubstituted C.sub.5-C.sub.60
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.60 heterocyclic group,
xb11 may be 1, 2, or 3,
L.sub.301 may be selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenylene group, a substituted or unsubstituted
C.sub.6-C.sub.60 group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroarylene group, a substituted or
unsubstituted divalent non-aromatic condensed polycyclic group, and
a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group,
xb1 may be an integer selected from 0 to 5,
R.sub.301 may be selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.301)(Q.sub.302)(Q.sub.303), --N(Q.sub.301)(Q.sub.302),
--B(Q.sub.301)(Q.sub.302), --C(.dbd.O)(Q.sub.301),
--S(.dbd.O).sub.2(Q.sub.301), and
--P(.dbd.O)(Q.sub.301)(Q.sub.302), and
xb21 may be an integer selected from 1 to 5,
wherein Q.sub.301 to Q.sub.303 may be each independently selected
from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, and a
naphthyl group, but embodiments are not limited thereto.
In some embodiments, Ar.sub.301 in Formula 301 may be selected from
the group consisting of:
a naphthalene group, a fluorene group, a spiro-bifluorene group, a
benzofluorene group, a dibenzofluorene group, a phenalene group, a
phenanthrene group, an anthracene group, a fluoranthene group, a
triphenylene group, a pyrene group, a chrysene group, a naphthacene
group, a picene group, a perylene group, a pentaphene group, an
indenoanthracene group, a dibenzofuran group, and a
dibenzothiophene group; and
a naphthalene group, a fluorene group, a spiro-bifluorene group, a
benzofluorene group, a dibenzofluorene group, a phenalene group, a
phenanthrene group, an anthracene group, a fluoranthene group, a
triphenylene group, a pyrene group, a chrysene group, a naphthacene
group, a picene group, a perylene group, a pentaphene group, an
indenoanthracene group, a dibenzofuran group, and a
dibenzothiophene group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
wherein Q.sub.31 to Q.sub.33 may be each independently selected
from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, and a
naphthyl group, but embodiments are not limited thereto.
When xb11 in Formula 301 is 2 or greater, a plurality of
Ar.sub.301(s) may be bound to a respective one another via a single
bond.
In one or more embodiments, the compound represented by Formula 301
may be represented by Formula 301-1 or 301-2:
##STR00023##
wherein, in Formulae 301-1 to 301-2,
A.sub.301 to A.sub.304 may be each independently selected from a
benzene group, a naphthalene group, a phenanthrene group, a
fluoranthene group, a triphenylene group, a pyrene group, a
chrysene group, a pyridine group, a pyrimidine group, an indene
group, a fluorene group, a spiro-bifluorene group, a benzofluorene
group, a dibenzofluorene group, an indole group, a carbazole group,
a benzocarbazole group, a dibenzocarbazole group, a furan group, a
benzofuran group, a dibenzofuran group, a naphthofuran group, a
benzonaphthofuran group, a dinaphthofuran group, a thiophene group,
a benzothiophene group, a dibenzothiophene group, a
naphthothiophene group, a benzonaphthothiophene group, and a
dinaphthothiophene group,
X.sub.301 may be O, S, or N-[(L.sub.304).sub.xb4-R.sub.304],
R.sub.311 to R.sub.314 may be each independently selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
xb22 and xb23 may be each independently 0, 1, or 2,
descriptions of L.sub.301, xb1, R.sub.301, and Q.sub.31 to Q.sub.33
may each independently be the same as those provided herein,
descriptions of L.sub.302 to L.sub.304 may be each independently
the same as the description provided herein in connection with
L.sub.301,
descriptions of xb2 to xb4 may be each independently the same as
the description provided herein in connection with xb1, and
descriptions of R.sub.302 to R.sub.304 may be each independently
the same as the description provided herein in connection with
R.sub.301.
In some embodiments, L.sub.301 to L.sub.304 in Formulae 301, 301-1,
and 301-2 may be each independently selected from the group
consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, an
azacarbazolyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
wherein Q.sub.31 to Q.sub.33 may be the same as those described
herein.
In some embodiments, R.sub.301 to R.sub.304 in Formulae 301, 301-1,
and 301-2 may be each independently selected from the group
consisting of:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, an
azacarbazolyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
wherein Q.sub.31 to Q.sub.33 may be the same as those described
herein.
In one or more embodiments, the host may include an alkaline earth
metal complex. For example, the host may be selected from a
beryllium (Be) complex (e.g., Compound H55 illustrated below), a
magnesium (Mg) complex, and a zinc (Zn) complex.
The host may include at least one selected from
9,10-di(2-naphthyl)anthracene (ADN),
2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),
9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),
4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP),
1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene
(TCP), and Compounds H1 to H55, but embodiments are not limited
thereto:
##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028##
##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033##
##STR00034## ##STR00035## Phosphorescent Dopant Included in an
Emission Layer of the Organic Layer 150
The phosphorescent dopant may include an organometallic complex
represented by Formula 401:
##STR00036##
wherein, in Formulae 401 and 402,
M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),
osmium
(Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),
terbium (Tb), rhodium (Rh), and thulium (Tm),
L.sub.401 may be selected from ligands represented by Formula 402,
and xc1 may be 1, 2, or 3; when xc1 is 2 or greater, a plurality of
L.sub.401(s) may be identical to or different from each other,
L.sub.402 may be an organic ligand, and xc2 may be an integer
selected from 0 to 4; when xc2 is 2 or greater, a plurality of
L.sub.402(s) may be identical to or different from each other,
X.sub.401 to X.sub.404 may be each independently nitrogen (N) or
carbon (C),
X.sub.401 and X.sub.403 are bound to each other via a single bond
or a double bond;
X.sub.402 and X.sub.404 are bound to each other via a single bond
or a double bond,
A.sub.401 and A.sub.402 may be each independently a
C.sub.5-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60
heterocyclic group,
X.sub.405 may be a single bond, *--O--*', *--C(.dbd.O)--*',
*--N(Q.sub.411)-*', *--C(Q.sub.411)(Q.sub.412)-*',
*--C(Q.sub.411)=C(Q.sub.412)-*', *--C(Q.sub.411)=*', or
*.dbd.C(Q.sub.411)=*', wherein Q.sub.411 and Q.sub.412 may be each
independently selected from hydrogen, deuterium, a C.sub.1-C.sub.20
alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a
biphenyl group, a terphenyl group, and a naphthyl group,
X.sub.406 may be a single bond, O, or S,
R.sub.401 and R.sub.402 may be each independently selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.20
alkyl group, a substituted or unsubstituted C.sub.1-C.sub.20 alkoxy
group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group, a
substituted or unsubstituted monovalent non-aromatic condensed
heteropolycyclic group, --Si(Q.sub.401)(Q.sub.402)(Q.sub.403),
--N(Q.sub.401)(Q.sub.402), --B(Q.sub.401)(Q.sub.402),
--C(.dbd.O)(Q.sub.401), --S(.dbd.O).sub.2(Q.sub.401), and
--P(.dbd.O)(Q.sub.401)(Q.sub.402), wherein Q.sub.401 to Q.sub.403
may be each independently selected from a C.sub.1-C.sub.10 alkyl
group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.6-C.sub.20 aryl
group, and a C.sub.1-C.sub.20 heteroaryl group,
xc11 and xc12 may be each independently an integer selected from 0
to 10, and
* and *' in Formula 402 may each independently indicate a binding
site to M in Formula 401.
According to an embodiment, A.sub.401 and A.sub.402 in Formula 402
may be each independently selected from a benzene group, a
naphthalene group, a fluorene group, a spiro-bifluorene group, an
indene group, a pyrrole group, a thiophene group, a furan group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, a quinoline
group, an isoquinoline group, a benzoquinoline group, a quinoxaline
group, a quinazoline group, a carbazole group, a benzoimidazole
group, a benzofuran group, a benzothiophene group, an
isobenzothiophene group, a benzoxazole group, an isobenzoxazole
group, a triazole group, a tetrazole group, an oxadiazole group, a
triazine group, a dibenzofuran group, and a dibenzothiophene
group.
In one or more embodiments, in Formula 402, i) X.sub.401 may be
nitrogen, and X.sub.402 may be carbon, or ii) X.sub.401 and
X.sub.402 may both be nitrogen.
According to some embodiments, R.sub.401 and R.sub.402 in Formula
402 may be each independently selected from the group consisting
of:
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a phenyl
group, a naphthyl group, a cyclopentyl group, a cyclohexyl group,
an adamantyl group, a norbornanyl group, and a norbornenyl
group;
a cyclopentyl group, a cyclohexyl group, an adamantyl group, a
norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl
group, a terphenyl group, a naphthyl group, a fluorenyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, a triazinyl group, a quinolinyl group, an
isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group;
a cyclopentyl group, a cyclohexyl group, an adamantyl group, a
norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl
group, a terphenyl group, a naphthyl group, a fluorenyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, a triazinyl group, a quinolinyl group, an
isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro
group, an amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
cyclopentyl group, a cyclohexyl group, an adamantyl group, a
norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl
group, a terphenyl group, a naphthyl group, a fluorenyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, a triazinyl group, a quinolinyl group, an
isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group; and
--Si(Q.sub.401)(Q.sub.402)(Q.sub.403), --N(Q.sub.401)(Q.sub.402),
--B(Q.sub.401)(Q.sub.402), --C_(.dbd.O) (Q.sub.401),
--S(.dbd.O).sub.2(Q.sub.401), and
--P(.dbd.O)(Q.sub.401)(Q.sub.402),
wherein Q.sub.401 to Q.sub.403 may be each independently selected
from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, and a naphthyl group, but
embodiments are not limited thereto.
In one or more embodiments, when xc1 in Formula 401 is 2 or
greater, two A.sub.401(s) in a plurality of L.sub.401(s) may
optionally be bound to each other via X.sub.407 as a linking group,
and two A.sub.402(s) may optionally be bound to each other via
X.sub.408 as a linking group (see e.g., Compounds PD1 to PD4 and
PD7). X.sub.407 and X.sub.408 may be each independently selected
from a single bond, *--O--*', *--C(.dbd.O)--*', *--N(Q.sub.413)-*',
*--C(Q.sub.413)(Q.sub.414)-*' or *--C(Q.sub.413)=C(Q.sub.414)-*'
wherein, Q.sub.413 and Q.sub.414 may be each independently selected
from hydrogen, deuterium, a C.sub.1-C.sub.20 alkyl group, a
C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a
terphenyl group, and a naphthyl group, but embodiments are not
limited thereto.
L.sub.402 in Formula 401 may be any suitable monovalent, divalent,
or trivalent organic ligand. In some embodiments, L.sub.402 may be
selected from halogen, diketone (e.g., acetylacetonate), a
carboxylic acid (e.g., picolinate), --C(.dbd.O), isonitrile, --CN,
and phosphorus (e.g., phosphine and/or phosphite), but embodiments
are not limited thereto.
In some embodiments, the phosphorescent dopant may include, for
example, at least one selected from Compounds PD1 to PD25, but
embodiments are not limited thereto:
##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041##
Fluorescent Dopant in Emission Layer
The fluorescent dopant may include an arylamine compound or a
styrylamine compound.
In some embodiments, the fluorescent dopant may include a compound
represented by Formula 501:
##STR00042##
wherein, in Formula 501,
Ar.sub.501 may be a substituted or unsubstituted C.sub.5-C.sub.60
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.60 heterocyclic group,
L.sub.501 to L.sub.503 may be each independently selected from a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group,
a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene
group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkenylene group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroarylene group, a substituted
or unsubstituted divalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group,
xd1 to xd3 may be each independently an integer selected from 0 to
3,
R.sub.501 and R.sub.502 may be each independently selected from a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl
group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenyl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted
monovalent non-aromatic condensed polycyclic group, and a
substituted or unsubstituted monovalent non-aromatic condensed
heteropolycyclic group, and
xd4 may be an integer selected from 1 to 6.
In some embodiments, Ar.sub.5o1 in Formula 501 may be selected from
the group consisting of:
a naphthalene group, a heptalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, a naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, and an
indenophenanthrene group; and
a naphthalene group, a heptalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, a naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, and an
indenophenanthrene group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
In one or more embodiments, L.sub.501 to L.sub.503 in Formula 501
may be each independently selected from the group consisting
of:
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group,
a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group,
a terphenyl group, a naphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl
group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
perylenyl group, a pentaphenyl group, a hexacenyl group, a
pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl
group, an indolyl group, an isoindolyl group, a benzofuranyl group,
a benzothiophenyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl
group.
According to some embodiments, R.sub.501 and R.sub.501 in Formula
502 may be each independently selected from the group consisting
of:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, and a pyridinyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, and a pyridinyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, and
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
wherein Q.sub.31 to Q.sub.33 may each independently selected from a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, and a naphthyl
group.
In one or more embodiments, xd4 in Formula 501 may be 2, but
embodiments are not limited thereto.
In some embodiments, the fluorescent dopant may be selected from
Compounds FD1 to FD22:
##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047##
##STR00048##
In some embodiments, the fluorescent dopant may be selected from
the compounds below, but embodiments are not limited thereto:
##STR00049## Electron Transport Region in Organic Layer 150
The electron transport region may have i) a single-layered
structure including a single layer including a single material, ii)
a single-layered structure including a single layer including a
plurality of different materials, or iii) a multi-layered structure
having a plurality of layers including a plurality of different
materials.
The electron transport region may include at least one selected
from a buffer layer, a hole blocking layer, an electron control
layer, an electron transport layer, and an electron injection
layer, but is not limited thereto.
In some embodiments, the electron transport region may have a
structure of electron transport layer/electron injection layer, a
structure of hole blocking layer/electron transport layer/electron
injection layer, a structure of electron control layer/electron
transport layer/electron injection layer, or a structure of buffer
layer/electron transport layer/electron injection layer, wherein
the layers of these structures are sequentially stacked in these
stated orders on an emission layer. However, the structure of the
electron transport region is not limited thereto.
The electron transport region (e.g., a buffer layer, a hole
blocking layer, an electron control layer, and/or an electron
transport layer in the electron transport region) may include a
metal-free compound containing at least one .pi. electron-depleted
nitrogen-containing ring.
The term ".pi. electron-depleted nitrogen-containing ring" as used
herein may refer to a C.sub.1-C.sub.60 heterocyclic group having at
least one *--N.dbd.*' moiety as a ring-forming moiety.
For example, the ".pi. electron-depleted nitrogen-containing ring"
may be i) a 5-membered to 7-membered heteromonocyclic group having
at least one *--N.dbd.*' moiety, ii) a heteropolycyclic group in
which two or more 5-membered to 7-membered heteromonocyclic groups
each having at least one *--N.dbd.*' moiety are condensed (e.g.,
fused), or iii) a heteropolycyclic group in which at least one
5-membered to 7-membered heteromonocyclic group having at least one
*--N.dbd.*' moiety, is condensed (e.g., fused) with at least one
C.sub.5-C.sub.60 carbocyclic group.
Non-limiting examples of the .pi. electron-depleted
nitrogen-containing ring may include an imidazole, a pyrazole, a
thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a
pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a
quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a
naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a
phenanthridine, an acridine, a phenanthroline, a phenazine, a
benzimidazole, an isobenzothiazole, a benzoxazole, an
isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine,
thiadiazole, an imidazopyridine, an imidazopyrimidine, and an
azacarbazole, but are not limited thereto.
In some embodiments, the electron transport region may include a
compound represented by Formula 601:
[Ar.sub.601].sub.xe11-[(L.sub.601).sub.xe1-R.sub.601].sub.xe21,
Formula 601
wherein, in Formula 601,
Ar.sub.601 may be a substituted or unsubstituted C.sub.5-C.sub.60
carbocyclic group or a substituted or unsubstituted
C.sub.1-C.sub.60 heterocyclic group,
xe11 may be 1, 2, or 3,
L.sub.601 may be selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenylene group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroarylene group, a substituted or
unsubstituted divalent non-aromatic condensed polycyclic group, and
a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group,
xe1 may be an integer selected from 0 to 5,
R.sub.601 may be selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.601)(Q.sub.602)(Q.sub.603), --C(.dbd.O)(Q.sub.601),
--S(.dbd.O).sub.2(Q.sub.601), and
--P(.dbd.O)(Q.sub.601)(Q.sub.602),
wherein Q.sub.601 to Q.sub.603 may be each independently a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, or a naphthyl
group, and
xe21 may be an integer selected from 1 to 5.
In some embodiments, at least one selected from the xe11 number of
Ar.sub.601(s) and the xe21 number of R.sub.601(s) may include a
.pi. electron-depleted nitrogen-containing ring.
In some embodiments, ring Ar.sub.601 in Formula 601 may be selected
from the group consisting of:
a benzene group, a naphthalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, a naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, a
dibenzofuran group, a dibenzothiophene group, a carbazole group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, an indazole
group, a purine group, a quinoline group, an isoquinoline group, a
benzoquinoline group, a phthalazine group, a naphthyridine group, a
quinoxaline group, a quinazoline group, a cinnoline group, a
phenanthridine group, an acridine group, a phenanthroline group, a
phenazine group, a benzoimidazole group, an iso-benzothiazole
group, a benzoxazole group, an isobenzoxazole group, a triazole
group, a tetrazole group, an oxadiazole group, a triazine group, a
thiadiazole group, an imidazopyridine group, an imidazopyrimidine
group, and indenoquinoline group; and
a benzene group, a naphthalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, a naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, a
dibenzofuran group, a dibenzothiophene group, a carbazole group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, an indazole
group, a purine group, a quinoline group, an isoquinoline group, a
benzoquinoline group, a phthalazine group, a naphthyridine group, a
quinoxaline group, a quinazoline group, a cinnoline group, a
phenanthridine group, an acridine group, a phenanthroline group, a
phenazine group, a benzoimidazole group, an iso-benzothiazole
group, a benzoxazole group, an isobenzoxazole group, a triazole
group, a tetrazole group, an oxadiazole group, a triazine group, a
thiadiazole group, an imidazopyridine group, an imidazopyrimidine
group, and indenoquinoline group, each substituted with at least
one selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazino
group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a
C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a
terphenyl group, a naphthyl group,
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --S(.dbd.O).sub.2(Q.sub.31),
and --P(.dbd.O)(Q.sub.31)(Q.sub.32),
wherein Q.sub.31 to Q.sub.33 may be each independently selected
from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, and a
naphthyl group.
When xe11 in Formula 601 is 2 or greater, a plurality of
Ar.sub.601(s) may be bound to each other via a single bond.
In one embodiment, Ar.sub.601 in Formula 601 may be an anthracene
group.
In some embodiments, the compound represented by Formula 601 may be
represented by Formula 601-1:
##STR00050##
wherein, in Formula 601-1,
X.sub.614 may be N or C(R.sub.614), X.sub.615 may be N or
C(R.sub.615), X.sub.616 may be N or C(R.sub.616), and at least one
selected from X.sub.614 to X.sub.616 may be N,
descriptions of L.sub.611 to L.sub.613 may be each independently
the same as the description provided herein in connection with
L.sub.601,
descriptions of xe611 to xe613 may be each independently the same
as the description provided herein in connection with xe1,
descriptions of R.sub.611 to R.sub.613 may be each independently
substantially the same as the description provided herein in
connection with R.sub.601, and
R.sub.614 to R.sub.616 may be each independently selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
In one embodiment, L.sub.601 and L.sub.611 to L.sub.613 in Formulae
601 and 601-1 may be each independently selected from the group
consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzoimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group, but embodiments are not limited thereto.
In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601
and 601-1 may be each independently selected from 0, 1, and 2.
In some embodiments, R.sub.601 and R.sub.611 to R.sub.613 in
Formulae 601 and 601-1 may be each independently selected from the
group consisting of:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group; and
--S(.dbd.O).sub.2(Q.sub.601) and
--P(.dbd.O)(Q.sub.601)(Q.sub.602),
wherein Q.sub.601 and Q.sub.602 may be each independently the same
as described herein.
The electron transport region may include at least one compound
selected from Compounds ET1 to ET36, but embodiments are not
limited thereto:
##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055##
##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060##
##STR00061##
In one or more embodiments, the electron transport region may
include at least one compound selected from
2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),
4,7-diphenyl-1,10-phenanthroline (Bphen), Alq.sub.3, BAlq,
3-(Biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole
(TAZ), and NTAZ:
##STR00062##
The thickness of the buffer layer, the hole blocking layer, and the
electron control layer may be each independently in a range of
about 20 .ANG. to about 1,000 .ANG.. When the thicknesses of the
buffer layer, the hole blocking layer, and the electron control
layer are each within any of these ranges, the electron transport
region may have excellent (or suitable) hole blocking
characteristics or electron control characteristics without a
substantial increase in driving voltage.
The thickness of the electron transport layer may be in a range of
about 100 .ANG. to about 1,000 .ANG., and in some embodiments,
about 150 .ANG. to about 500 .ANG.. When the thickness of the
electron transport layer is within any of these ranges, the
electron transport layer may have satisfactory (or suitable)
electron transport characteristics without a substantial increase
in driving voltage.
The electron transport region (e.g., the electron transport layer
in the electron transport region) may further include, in addition
to the materials described above, a metal-containing material.
The metal-containing material may include at least one selected
from an alkali metal complex and an alkaline earth metal complex.
The alkali metal complex may include a metal ion selected from an
Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion, and the alkaline
earth metal complex may include a metal ion selected from a Be ion,
a Mg ion, a Ca ion, an Sr ion, and a Ba ion. Ligands respectively
coordinated with the metal ion of the alkali metal complex or the
alkaline earth metal complex may be each independently selected
from a hydroxyquinoline, a hydroxyisoquinoline, a
hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine,
a hydroxyphenyl oxazole, a hydroxyphenyl thiazole, a
hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, a
hydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a
hydroxyphenyl benzothiazole, a bipyridine, a phenanthroline, and a
cyclopentadiene, but embodiments are not limited thereto.
In some embodiments, the metal-containing material may include a Li
complex. The Li complex may include, for example, Compound ET-D1
(lithium quinolate, LiQ) and/or Compound ET-D2:
##STR00063##
The electron transport region may include an electron injection
layer that facilitates injection of electrons from the second
electrode 190. The electron injection layer may directly contact
the second electrode 190.
The electron injection layer may have i) a single-layered structure
including a single layer including a single material, ii) a
single-layered structure including a single layer including a
plurality of different materials, or iii) a multi-layered structure
having a plurality of layers including a plurality of different
materials.
The electron injection layer may include an alkali metal, an
alkaline earth metal, a rare-earth metal, an alkali metal compound,
an alkaline earth metal compound, a rare-earth metal compound, an
alkali metal complex, an alkaline earth metal complex, a rare-earth
metal complex, or a combination thereof.
The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one
embodiment, the alkali metal may be selected from Li, Na, and Cs.
In one or more embodiments, the alkali metal may be Li or Cs, but
is not limited thereto.
The alkaline earth metal may be selected from Mg, Ca, Sr, and
Ba.
The rare-earth metal may be selected from Sc, Y, Ce, Tb, Yb, Gd,
and Tb.
The alkali metal compound, the alkaline earth metal compound, and
the rare-earth metal compound may be each independently selected
from oxides and halides (e.g., fluorides, chlorides, bromides,
and/or iodines) of the alkali metal, the alkaline earth metal, and
the rare-earth metal, respectively.
In some embodiments, the alkali metal compound may be selected from
alkali metal oxides (such as Li.sub.2O, Cs.sub.2O, and/or K.sub.2O)
and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI,
and/or KI). In one embodiment, the alkali metal compound may be
selected from LiF, Li.sub.2O, NaF, LiI, NaI, CsI, and KI, but is
not limited thereto.
The alkaline earth metal compound may be selected from alkaline
earth metal compounds, such as BaO, SrO, CaO, Ba.sub.xSr.sub.1-xO
(wherein 0<x<1), and/or Ba.sub.xCa.sub.1-xO (wherein
0<x<1). In one embodiment, the alkaline earth metal compound
may be selected from BaO, SrO, and CaO, but is not limited
thereto.
The rare-earth metal compound may be selected from YbF.sub.3,
ScF.sub.3, ScO.sub.3, Y.sub.2O.sub.3, Ce.sub.2O.sub.3, GdF.sub.3,
and TbF.sub.3. In one embodiment, the rare-earth metal compound may
be selected from YbF.sub.3, ScF.sub.3, TbF.sub.3, YbI.sub.3,
ScI.sub.3, and TbI.sub.3, but is not limited thereto.
The alkali metal complex, the alkaline earth metal complex, and the
rare-earth metal complex may include an alkali metal ion, and
alkaline earth metal ion, and a rare-earth metal ion, respectively,
as described above, and ligands respectively coordinated with the
metal ion of the alkali metal complex, the alkaline earth metal
complex, and the rare-earth metal complex may each independently be
selected from a hydroxyquinoline, a hydroxyisoquinoline, a
hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine,
a hydroxyphenyl oxazole, a hydroxyphenyl thiazole, a
hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, a
hydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a
hydroxyphenyl benzothiazole, a bipyridine, a phenanthroline, and a
cyclopentadiene, but are not limited thereto.
The electron injection layer may include an alkali metal, an
alkaline earth metal, a rare-earth metal, an alkali metal compound,
an alkaline earth metal compound, a rare-earth metal compound, an
alkali metal complex, an alkaline earth metal complex, an
rare-earth metal complex, or a combination thereof, as described
above. In one or more embodiments, the electron injection layer may
further include an organic material. When the electron injection
layer further includes an organic material, an alkali metal, an
alkaline earth metal, a rare-earth metal, an alkali metal compound,
an alkaline earth metal compound, a rare-earth metal compound, an
alkali metal complex, an alkaline earth metal complex, a rare-earth
metal complex, or a combination thereof may be homogeneously or
non-homogeneously dispersed in a matrix including the organic
material.
A thickness of the electron injection layer may be in a range of
about 1 .ANG. to about 100 .ANG., and in some embodiments, about 3
.ANG. to about 90 .ANG.. When the thickness of the electron
injection layer is within any of these ranges, the electron
injection layer may have satisfactory (or suitable) electron
injection characteristics without a substantial increase in driving
voltage.
Second Electrode 190
The second electrode 190 may be disposed on the organic layer 150.
The second electrode 190 may be a cathode, which is an electron
injection electrode, and in this regard, a material for forming the
second electrode 190 may be selected from a metal, an alloy, an
electrically conductive compound, and a combination thereof, each
having a relatively low work function.
The second electrode 190 may include at least one selected from
lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al),
aluminum-lithium (Al--Li), calcium (Ca), magnesium-indium (Mg--In),
magnesium-silver (Mg--Ag), ITO, and IZO, but is not limited
thereto. The second electrode 190 may be a transmissive electrode,
a semi-transmissive electrode, or a reflective electrode.
The second electrode 190 may have a single-layered structure, or a
multi-layered structure including two or more layers.
Description of FIGS. 4 to 6
An organic light-emitting device 20 represented by FIG. 4 includes
a first capping layer 210, the first electrode 110, the organic
layer 150, and the second electrode 190 sequentially stacked in
this stated order. An organic light-emitting device 30 represented
by FIG. 5 includes the first electrode 110, the organic layer 150,
the second electrode 190, and a second capping layer 220
sequentially stacked in this stated order. An organic
light-emitting device 40 represented by FIG. 6 includes the first
capping layer 210, the first electrode 110, the organic layer 150,
the second electrode 190, and the second capping layer 220
sequentially stacked in this stated order.
Regarding FIGS. 4 to 6, descriptions of the first electrode 110,
the organic layer 150, and the second electrode 190 may be each
independently the same as those provided herein in connection with
FIG. 1.
In the organic light-emitting devices 20 and 40, light emitted from
the emission layer in the organic layer 150 may pass through the
first electrode 110 (which may be a semi-transmissive electrode or
a transmissive electrode) and through the first capping layer 210
to the outside. In the organic light-emitting devices 30 and 40,
light emitted from the emission layer in the organic layer 150 may
pass through second electrode 190 (which may be a semi-transmissive
electrode or a transmissive electrode) and through the second
capping layer 220 to the outside.
The first capping layer 210 and the second capping layer 220 may
improve the external luminous efficiency based on the principle of
constructive interference.
The first capping layer 210 and the second capping layer 220 may be
each independently a capping layer including an organic material,
an inorganic capping layer including an inorganic material, or a
composite capping layer including an organic material and an
inorganic material.
At least one selected from the first capping layer 210 and the
second capping layer 220 may include at least one material selected
from carbocyclic compounds, heterocyclic compounds, amine-based
compounds, porphyrin derivatives, phthalocyanine derivatives,
naphthalocyanine derivatives, alkali metal-based complexes, and
alkaline earth metal-based complexes. The carbocyclic compound, the
heterocyclic compound, and the amine-based compound may each
independently be optionally substituted with a substituent
containing at least one element selected from O, N, S, selenium
(Se), silicon (Si), fluorine (F), chlorine (CI), bromine (Br), and
iodine (I). In one embodiment, at least one selected from the first
capping layer 210 and the second capping layer 220 may include an
amine-based compound.
In one embodiment, at least one selected from the first capping
layer 210 and the second capping layer 220 may include the compound
represented by Formula 201 or the compound represented by Formula
202.
In one or more embodiments, at least one selected from the first
capping layer 210 and the second capping layer 220 may include a
compound selected from Compounds HT28 to HT33 and Compounds CP1 to
CP5, but is not limited thereto:
##STR00064##
Hereinbefore, the organic light-emitting device according to an
embodiment has been described in connection with FIGS. 1-6.
However, embodiments are not limited thereto.
The layers constituting the hole transport region, the emission
layer, and the layers constituting the electron transport region
may be formed in a specific region using one or more suitable
methods such vacuum deposition, spin coating, casting,
Langmuir-Blodgett (LB) deposition, ink-jet printing,
laser-printing, and/or laser-induced thermal imaging (LITI).
When the layers constituting the hole transport region, the
emission layer, and the layers constituting the electron transport
region are each independently formed by vacuum deposition, the
vacuum deposition may be performed at a deposition temperature of
about 100 to about 500.degree. C., at a vacuum degree of about
10.sup.-8 to about 10.sup.-3 torr, and at a deposition rate of
about 0.01 to about 100 .ANG./sec, depending on the compound to be
included in each layer and the structure of each layer to be
formed.
When the layers constituting the hole transport region, the
emission layer, the and layers constituting the electron transport
region are each independently formed by spin coating, the spin
coating may be performed at a coating rate of about 2,000
revolutions per minute (rpm) to about 5,000 rpm and at a heat
treatment temperature of about 80.degree. C. to 200.degree. C.,
depending on the compound to be included in each layer and the
structure of each layer to be formed.
General Definition of Substituents
The term "C.sub.1-C.sub.60 alkyl group" as used herein may refer to
a linear or branched aliphatic hydrocarbon monovalent group having
1 to 60 carbon atoms. Non-limiting examples thereof may include a
methyl group, an ethyl group, a propyl group, an iso-butyl group, a
sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl
group, and a hexyl group. The term "C.sub.1-C.sub.60 alkylene
group" as used herein may refer to a divalent group having the same
structure as the C.sub.1-C.sub.60 alkyl group.
The term "C.sub.2-C.sub.60 alkenyl group" as used herein may refer
to a hydrocarbon group having at least one carbon-carbon double
bond at one or more positions along the hydrocarbon chain of the
C.sub.2-C.sub.60 alkyl group (e.g., in the middle and/or at either
terminus of the C.sub.2-C.sub.60 alkyl group). Non-limiting
examples thereof may include an ethenyl group, a propenyl group,
and a butenyl group. The term "C.sub.2-C.sub.60 alkenylene group"
as used herein may refer to a divalent group having the same
structure as the C.sub.2-C.sub.60 alkenyl group.
The term "C.sub.2-C.sub.60 alkynyl group" as used herein may refer
to a hydrocarbon group having at least one carbon-carbon triple
bond at one or more positions along the hydrocarbon chain of the
C.sub.2-C.sub.60 alkyl group (e.g., in the middle and/or at either
terminus of the C.sub.2-C.sub.60 alkyl group). Non-limiting
examples thereof may include an ethynyl group and a propynyl group.
The term "C.sub.2-C.sub.60 alkynylene group" as used herein may
refer to a divalent group having the same structure as the
C.sub.2-C.sub.60 alkynyl group.
The term "C.sub.1-C.sub.60 alkoxy group" as used herein may refer
to a monovalent group represented by --OA.sub.101 (where A.sub.101
is the C.sub.1-C.sub.60 alkyl group). Non-limiting examples thereof
may include a methoxy group, an ethoxy group, and an isopropyloxy
group.
The term "C.sub.3-C.sub.10 cycloalkyl group" as used herein may
refer to a monovalent saturated hydrocarbon monocyclic group
including 3 to 10 carbon atoms. Non-limiting examples thereof may
include a cyclopropyl group, a cyclobutyl group, a cyclopentyl
group, a cyclohexyl group, and a cycloheptyl group. The term
"C.sub.3-C.sub.10 cycloalkylene group" as used herein may refer to
a divalent group having the same structure as the C.sub.3-C.sub.10
cycloalkyl group.
The term "C.sub.1-C.sub.10 heterocycloalkyl group" as used herein
may refer to a monovalent monocyclic group including at least one
heteroatom selected from N, O, Si, P, and S as a ring-forming atom
and 1 to 10 carbon atoms. Non-limiting examples thereof may include
a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a
tetrahydrothiophenyl group. The term "C.sub.1-C.sub.10
heterocycloalkylene group" as used herein may refer to a divalent
group having the same structure as the C.sub.1-C.sub.10
heterocycloalkyl group.
The term "C.sub.3-C.sub.10 cycloalkenyl group" as used herein may
refer to a monovalent monocyclic group that has 3 to 10 carbon
atoms and at least one double bond in its ring, and is not
aromatic. Non-limiting examples thereof may include a cyclopentenyl
group, a cyclohexenyl group, and a cycloheptenyl group. The term
"C.sub.3-C.sub.10 cycloalkenylene group" as used herein may refer
to a divalent group having the same structure as the
C.sub.3-C.sub.10 cycloalkenyl group.
The term "C.sub.1-C.sub.10 heterocycloalkenyl group" as used herein
may refer to a monovalent monocyclic group including at least one
heteroatom selected from N, O, Si, P, and S as a ring-forming atom,
1 to 10 carbon atoms, and at least one double bond in its ring.
Non-limiting examples of the C.sub.1-C.sub.10 heterocycloalkenyl
group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a
2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The
term "C.sub.1-C.sub.10 heterocycloalkylene group" as used herein
may refer to a divalent group having the same structure as the
C.sub.1-C.sub.10 heterocycloalkyl group.
The term "C.sub.6-C.sub.60 aryl group" as used herein may refer to
an aromatic monovalent group having 6 to 60 carbon atoms. The term
"C.sub.6-C.sub.60 arylene group" as used herein may refer to an
aromatic divalent group having 6 to 60 carbon atoms. Non-limiting
examples of the C.sub.6-C.sub.60 aryl group may include a phenyl
group, a naphthyl group, an anthracenyl group, a phenanthrenyl
group, a pyrenyl group, and a chrysenyl group. When the
C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group
each independently include a plurality of rings, the respective
rings may be fused to each other.
The term "C.sub.1-C.sub.60 heteroaryl group" as used herein may
refer to a monovalent group having a heterocyclic aromatic system
that has at least one heteroatom selected from N, O, Si, P, and S
as a ring-forming atom and 1 to 60 carbon atoms. The term
"C.sub.1-C.sub.60 heteroarylene group" as used herein may refer to
a divalent group having a heterocyclic aromatic system including at
least one heteroatom selected from N, O, Si, P, and S as a
ring-forming atom and 1 to 60 carbon atoms. Non-limiting examples
of the C.sub.1-C.sub.60 heteroaryl group may include a pyridinyl
group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group,
a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60
heteroarylene group each independently include a plurality of
rings, the respective rings may be fused to each other.
The term "C.sub.6-C.sub.60 aryloxy group" as used herein may refer
to a group represented by --OA.sub.102 (where A.sub.102 is the
C.sub.6-C.sub.60 aryl group). The term "C.sub.6-C.sub.60 arylthio
group" as used herein may refer to a group represented by
--SA.sub.103 (where A.sub.103 is the C.sub.6-C.sub.60 aryl
group).
The term "monovalent non-aromatic condensed polycyclic group" as
used herein may refer to a monovalent group that has a plurality of
rings condensed (e.g., fused) to each other, and has only carbon
atoms (e.g., 8 to 60 carbon atoms) as ring forming atoms, wherein
the molecular structure as a whole is non-aromatic (e.g., does not
have overall aromaticity). A non-limiting example of the monovalent
non-aromatic condensed polycyclic group may be a fluorenyl group.
The term "divalent non-aromatic condensed polycyclic group" as used
herein may refer to a divalent group having the same structure as
the monovalent non-aromatic condensed polycyclic group.
The term "monovalent non-aromatic condensed heteropolycyclic group"
as used herein may refer to a monovalent group that has two or more
rings condensed (e.g., fused) with each other, and has at least one
heteroatom selected from N, O, Si, P, and S as a ring-forming atom,
other than carbon atoms (e.g., 1 to 60 carbon atoms), wherein the
molecular structure as a whole is non-aromatic (e.g., does not have
overall aromaticity). A non-limiting example of the monovalent
non-aromatic condensed heteropolycyclic group may be a carbazolyl
group. The term "divalent non-aromatic condensed heteropolycyclic
group" as used herein may refer to a divalent group having the same
structure as the monovalent non-aromatic condensed
hetero-polycyclic group.
The term "C.sub.5-C.sub.60 carbocyclic group" as used herein may
refer to a monocyclic or polycyclic group having 5 to 60 carbon
atoms only as ring-forming atoms. The term "C.sub.5-C.sub.60
carbocyclic group" as used herein may refer to an aromatic
carbocyclic group or a non-aromatic carbocyclic group. The term
"C.sub.5-C.sub.60 carbocyclic group" as used herein may refer to a
ring (such as a benzene group), a monovalent group (such as a
phenyl group), or a divalent group (such as a phenylene group). In
one or more embodiments, depending on the number of substituents
connected to the C.sub.5-C.sub.60 carbocyclic group, the
C.sub.5-C.sub.60 carbocyclic group may be a trivalent group or a
quadrivalent group.
The term "C.sub.1-C.sub.60 heterocyclic group" as used herein may
refer to a group having the same structure as a C.sub.1-C.sub.60
carbocyclic group, except that as a ring-forming atom, at least one
heteroatom selected from N, O, Si, P, and S is used in addition to
carbon atoms (e.g., 1 to 60 carbon atoms).
In the present specification, at least one of substituents of the
substituted C.sub.5-C.sub.60 group, substituted C.sub.1-C.sub.60
heterocyclic group, substituted C.sub.3-C.sub.10 cycloalkylene
group, substituted C.sub.1-C.sub.10 heterocycloalkylene group,
substituted C.sub.3-C.sub.1 cycloalkenylene group, substituted
C.sub.1-C.sub.10 heterocycloalkenylene group, substituted
C.sub.6-C.sub.60 group, substituted C.sub.1-C.sub.60 heteroarylene
group, substituted divalent non-aromatic condensed polycyclic
group, substituted divalent non-aromatic condensed heteropolycyclic
group, substituted C.sub.1-C.sub.60 alkyl group, substituted
C.sub.2-C.sub.60 alkenyl group, substituted C.sub.2-C.sub.60
alkynyl group, substituted C.sub.1-C.sub.60 alkoxy group,
substituted C.sub.3-C.sub.10 cycloalkyl group, substituted
C.sub.1-C.sub.10 heterocycloalkyl group, substituted
C.sub.3-C.sub.10 cycloalkenyl group, substituted C.sub.1-C.sub.10
heterocycloalkenyl group, substituted C.sub.6-C.sub.60 aryl group,
substituted C.sub.6-C.sub.60 aryloxy group, substituted
C.sub.6-C.sub.60 arylthio group, substituted C.sub.1-C.sub.60
heteroaryl group, substituted monovalent non-aromatic condensed
polycyclic group, and substituted monovalent non-aromatic condensed
heteropolycyclic group may be selected from the group consisting
of:
deuterium(-D), --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60
group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60
alkoxy group;
a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a
C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro
group, an amidino group, a hydrazino group, a hydrazono group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group,
--Si(Q.sub.11)(Q.sub.12)(Q.sub.13), --N(Q.sub.11)(Q.sub.12),
--B(Q.sub.11)(Q.sub.12), --C(.dbd.O)(Q.sub.11),
--S(.dbd.O).sub.2(Q.sub.11), and
--P(.dbd.O)(Q.sub.11)(Q.sub.12);
a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group;
a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group,
a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group,
a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl
group, a C.sub.1-C.sub.10 heterocycloalkyl group, a
C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, a monovalent non-aromatic condensed
heteropolycyclic group, --Si(Q.sub.21)(Q.sub.22)(Q.sub.23),
--N(Q.sub.21)(Q.sub.22), --B(Q.sub.21)(Q.sub.22),
--C(.dbd.O)(Q.sub.21), --S(.dbd.O).sub.2(Q.sub.21), and
--P(.dbd.O)(Q.sub.21)(Q.sub.22); and
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
wherein Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to
Q.sub.33 may be each independently selected from hydrogen,
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl
group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy
group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, and a terphenyl
group.
The term "Ph" as used herein may refer to a phenyl group. The term
"Me" as used herein may refer to a methyl group. The term "Et" as
used herein may refer to an ethyl group. The term "ter-Bu" or
"Bu.sup.t" as used herein may refer to a tert-butyl group. The term
"OMe" as used herein may refer to a methoxy group, and "D" may
refer to deuterium.
The term "biphenyl group" as used herein may refer to a phenyl
group substituted with a phenyl group. The "biphenyl group" may be
a substituted phenyl group having a C.sub.6-C.sub.60 aryl group as
a substituent.
The term "terphenyl group" as used herein may refer to a phenyl
group substituted with a biphenyl group. The "terphenyl group" may
be a substituted phenyl group having a C.sub.6-C.sub.60 aryl group
substituted with a C.sub.6-C.sub.60 aryl group as a
substituent.
The symbols * and *' as used herein, unless defined otherwise,
refer to a binding site to an adjacent atom in a corresponding
formula.
Hereinafter a compound and an organic light-emitting device
according to one or more embodiments will be described in more
detail with reference to Synthesis Examples and Examples. The
expression "B was used instead of A" used in describing Synthesis
Examples may refer to a molar equivalent of A being identical to a
molar equivalent of B.
EXAMPLES
Example 1
As a substrate and an anode, a Corning 15 Ohms per square
centimeter (.OMEGA./cm.sup.2) (150 .ANG.) ITO glass substrate was
cut to a size of 50 millimeters (mm).times.50 mm.times.0.7 mm,
sonicated by using isopropyl alcohol and deionized water for 5
minutes, respectively, and cleaned by exposure to ultraviolet rays
with ozone. Then, the glass substrate was mounted on a vacuum
deposition device.
TATC (100 .ANG.), HAT-CN (50 .ANG.), and NPB (100 .ANG.) were
sequentially deposited on the ITO anode to form a hole transport
region.
HTL1 (100 .ANG.) was deposited on the hole transport region to form
a lower auxiliary layer, AND (ADN) and DPAVBi (the amount of DPAVBi
was 5 percent by weight (wt %)) were co-deposited at a total
thickness of 200 .ANG. to form an emission layer, and Alq (50
.ANG.) was deposited on the emission layer to form an upper
auxiliary layer, to thereby form a first emission unit.
Compound 1 and Yb (the amount of Yb was 2 wt %) were co-deposited
on the first emission unit at a total thickness of 150 .ANG. to
form an n-type charge generating layer, and HAT-CN (100 .ANG.) was
deposited on the n-type charge generating layer to form a p-type
charge generating layer, to thereby form a first charge generating
layer.
HTL1 (200 .ANG.) was deposited on the first charge generating layer
to form a lower auxiliary layer, CBP and (BT).sub.2Ir(acac) (the
amount of (BT).sub.2Ir(acac) was 15 wt %) were co-deposited on the
lower auxiliary layer at a total thickness of 200 .ANG. to form an
emission layer, and Alq (50 .ANG.) was deposited on the emission
layer to form an upper auxiliary layer, to thereby form a second
emission unit.
Compound 1 and Yb (the amount of Yb was 2 wt %) were co-deposited
on the second emission unit at a total thickness of 150 .ANG. to
form an n-type charge generating layer, and HAT-CN (100 .ANG.) was
deposited on the n-type charge generating layer to form a p-type
charge generating layer, to thereby form a second charge generating
layer.
NPB (100 .ANG.) and HTL1 (100 .ANG.) were sequentially deposited on
the second charge generating layer to form a lower auxiliary layer,
and AND (ADN) and DPAVBi (the amount of DPAVBi was 5 wt %) were
co-deposited on the lower auxiliary layer at a total thickness of
200 .ANG. to form an emission layer, to thereby form a third
emission unit.
Alq (50 .ANG.) was deposited on the third emission unit to form a
first electron transport layer, Compound 1 and Yb (the amount of Yb
was 2 wt %) were co-deposited on the first electron transport layer
at a total thickness of 200 .ANG. to form a second electron
transport layer, and LiF (15 .ANG.) was deposited on the second
electron transport layer to form an electron injection layer, to
thereby form an electron transport region.
Al (100 .ANG.) was deposited on the electron transport region to
form a cathode, thereby completing the manufacture of an organic
light-emitting device.
Examples 2 and 3 and Comparative Example 1
Organic light-emitting devices were manufactured in the same (or
substantially the same) manner as in Example 1, except that the
materials shown in Table 1 were used in the n-type charge
generating layer and in the second electron transport layer.
Evaluation Example 1
The driving voltage (V), efficiency (cd/A), and lifespan (T97) of
the organic light-emitting devices manufactured in Examples 1 to 3
and Comparative Example 1 were measured by using Keithley
source-measure unit (SMU) 236 and a luminance meter PR650. The
results thereof are shown in Table 1.
TABLE-US-00001 TABLE 1 n-type charge n-type charge generating
generating layer for the layer for the first charge second charge
Second electron Driving generating layer generating l